50 Weirdly Awesome Things to Do in Portland, Oregon

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From must-see sights to hidden gems, this is the ultimate list of things to do in Portland. This frequently updated Portland travel guide is packed with helpful information, local tips, and even a specially curated Portland map that will help you plan the perfect trip to this PNW city.

Things to Do in Portland | Two Wandering Soles

Portland is a city where weird is cool, craft beer is mainstream, and nature is intermingled throughout the city. It is everything the TV shows make it seem, and more.

Not only are there a ton of places to see and things to do in Portland, but there’s a certain vibe that we think you’ll love – we sure do!

Why trust us?

Being that we live in Oregon, we’ve visited Portland many, many times. (So many, in fact, that we’ve lost count!)

During each trip, we’ve explored many nooks and crannies that often get overlooked by first-time travelers, and we’ve taken lots of notes (and pictures!) along the way. And after each visit, we come back to this article and update it so that you know it’s one of the most up-to-date and comprehensive lists on the Internet!

famous white stag sign in Portland Oregon
We’ve been to Portland more times than we can count! Even our daughter, Juniper, had been to Portland 3 times before she was 6 months old. We’re here to share our top tips and favorite things to do in Stumptown!

If you’re planning a trip to Oregon’s biggest city, we’ve got you covered. This article has detailed descriptions of the best things to do in Portland – from the super quirky local secrets to can’t-miss top attractions.

Plus, we’ve packed this Portland travel guide full of tons of insider tips and local nuggets that will make your time in this city unforgettable. 

Plus, we even made a Portland map with all our favorite spots so you can keep it handy for your trip!

So pour yourself a craft beer and get ready to plan your own trip to this PNW metropolis. Be prepared to have lots of fun and to get a little weird… we’re talking about Portland, after all!

Portland Travel Guide Contents

For more tips and advice for planning your trip to Portland, jump to the following sections (or just keep scrolling to see it all!).

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Go ahead and grab your copy now. It’s free, so what do you have to lose?!

Top things to do in Portland, Oregon

If you’re looking for a quick list of the very best things to do in Portland, here you go:

  1. Go on a Portland food tour
  2. Hike to the “Witch’s Castle”
  3. Taste Portland’s best doughnuts
  4. Grab some grub at a food truck pod
  5. Tour the wineries in the Willamette Valley
  6. See the view from the Pittock Mansion
  7. Explore waterfalls in the Columbia River Gorge

Now your trip to Portland is almost planned!

But don’t stop here…

Watch our quick video on things to do in Portland, Oregon so you know exactly what to expect:

Want more ideas? Well, you are in for a treat, my friend, because this article is absolutely PACKED with the very best things to do in “Stumptown” plus all sorts of insider tips! 

Now let’s jump right in…

1. Go on a Portland food tour


We LOVE food. (Those all-caps are there for a reason.)

So it’s safe to say that this is one of our very favorite things to do in Portland, and we recommend taking a food tour this to just about all travelers!

We’ve found the best way to sample as much local cuisine as possible on our travels (without going totally broke or coming home with a double chin!) is by taking a food tour.

Not only do you get to try small portions of some of the city’s best foods (yes, please!), but you get an insider perspective of the foodie culture in that city, region or county.

We’ve gone on food tours all around the world – New York City, Bangkok, Kathmandu, Yogyakarta, Reykjavik, and Mexico City (to name just a few!), and had great experiences on all of them. So when we heard about this excellent food tour in Portland, we were totally on board.

Our experience

Lost Plate is a family-run company that offers food tours throughout China, Cambodia, and – you guessed it – Portland

Our guide, Michelle, is a native Portlandian and is super passionate about the food scene in her hometown. She was knowledgeable and excited to share tips with everyone on the tour (which happened to be 5 of us that night). 

**Find out how to get a discount on the tour below**


One thing we really enjoyed about this tour is that it has a good mix of different types of food and alcohol.

Just take a look at the stops:

  • Winery: We sampled 3 wines and shared a KILLER charcuterie platter
  • Handmade Pasta
  • Distillery: flight tasting of 5 different locally-made spirits
  • Bao Buns & a cocktail
  • Crepe: sweet or savory
  • Brewery: beer of our choice

We thought it was a truly great way to spend an evening in Portland. We’d recommend doing it early on in your trip so you can ask your guide for more tips on her favorite eateries and things to do around town. Plus, if you really love one of the stops, you can return later during your visit!

Lost Plate Portland food tours

Lost Plate offers a few different food tours in Portland:

Disclaimer: Lost Plate invited us on this tour as a complimentary experience. As always, all opinions are our own.

2. Order a Spanish Coffee at the oldest restaurant in Portland

Huber's Restaurant Portland Oregon

Serving patrons since 1879, Huber’s Cafe is a Portland institution. The historic building retains its old world charm, making patrons feel as if they’ve stepped back in time.

Known for their traditional turkey dinners and Spanish Coffees which are prepared tableside with flames and flair, Portland’s oldest restaurant is well worth a visit.

If you’re not familiar with Spanish Coffee, here’s what you can expect…

Rum and triple sec are poured into a sugar-rimmed glass before being lit on fire. The skilled bartender will swirl the flames to caramelize the sugar (so yummy!) before adding Kahlúa (coffee liquor), hot coffee, freshly whipped cream, and a dash of nutmeg. 

This drink can also be made iced, which would be refreshing on a sweltering summer’s day.

Fun Fact: Huber’s goes through more Kahlúa than any other bar in the United States!

It is definitely a “show” worth experiencing, and the resulting drinks are excellent. They’ll have you amped and ready to spend the rest of the evening exploring! Pssst! See #43 on this list for recs for a killer night out on the town!

Insider Tip: We recommend making reservations, especially if you’re visiting on a weekend. When we showed up, there was an hour wait.

3. Hike to the “Witch’s Castle”

Witch's Castle Hike Portland Oregon

Kinda creepy, really cool. This dilapidated house is located in the southernmost end of Portland’s Forest Park and is a sight to see!

Right next to a riverbank, this crumbling structure has been taken over by the forest, with vines creeping up the structure. It makes for an easy but interesting half-mile walk through the forest.

Good to know: Our photo of the Witch’s Castle is from 2017. It has since been graffitied and looks a bit different.

How to get there: It’s an easy half-mile hike down to a riverbed to get to the Witch’s Castle from the Upper Macleay Parking lot near the Portland Audubon Society. Or for a slightly longer jaunt, start from the Lower Macleay Parking lot at NW 30th and Upshur.

Psst! Check out our other favorite Portland hikes on our sister site!

Witch’s Castle history

The story behind it (the short version, at least!) is that Danford Balch, his wife and their 9 children lived in this house back in 1850. Danford wanted help clearing some nearby land, so he hired a helping hand, Mortimer Stump (that name just gives me goosebumps!). Well, Mortimer fell in love with 15-year Anna, which Big Daddy Danford did not approve of.

The young couple ran away to elope, but the next time Danford saw them together he drunkenly shot Mortimer in the head. Danford was arrested and later hanged (Trivia: the first legal hanging in Oregon territory), and Mary Jane continued to live in the property long after her husband was gone.

The structure was used for a few different purposes in the years after Mary Jane; like a park ranger station and a restroom for trail hikers. But after being badly damaged in a storm, it was abandoned and all but forgotten about until the 1980’s when high school students decided it would be a fun place to hold a kegger.

They affectionately started calling it the “Witch’s Castle”. And with its crumbly, moss-covered appearance, it’s easy to see why!

While we didn’t experience any strange things at the Witch’s Castle, it was a neat spot to see in the midst of a beautiful forest with few people around.

4. Visit the International Rose Test Garden (for free!)


Located in Portland’s Washington Park, the International Rose Test Garden has more than 10,000 rose bushes with just around 650 varieties. Who knew there were so many varieties of roses?! (We sure didn’t!)

The roses are in bloom between April and October, peaking in June.

This park is free to enter, and you can wander around breathing in the lovely aromas of roses in bloom. This is one of the most popular free things to do in Portland, so depending on the time of year and day of the week, it can get quite crowded.

Insider Tip: The Oregon Zoo and Hoyt Arboretum are just down the road from the Rose Garden in Washington Park.

5. Unwind in McMenamin’s Kennedy School (heated) outdoor soaking pool

McMenamin's Kennedy School Soaking Pool | Things to do in Portland, Oregon

If relaxing in a steamy outdoor pool with a drink in hand sounds like a good time to you, we’d make great friends! Also, listen up because we’ve got the perfect thing to squeeze into your Portland itinerary…

Nestled in the Woodlawn neighborhood of northeast Portland, the McMenamin’s Kennedy School Soaking Pool is a worthy escape from the bustle of downtown

Once an elementary school, this is quirky venue has been transformed into an entertainment center complete with a  hotel, restaurant, several bars, a movie theater, and yes, a soaking pool. Whew —  that was a lot of commas!

Insider Tip: Before changing into your bathing suit, head to the Courtyard Bar where you can grab a drink if you’d like to enjoy it in the warm embrace of the soaking pool. There is a pretty great cocktail list as well as a selection of McMenamin’s own beers.

The tepid water is comfortable on a chilly winter day, yet not so hot that you’ll need to get out and take a break every 5 minutes. It’s what Goldilocks would deem juuuust right

Turn on the jets for an ultra relaxing bathwater-meets-hot-tub experience. With tropical looking trees bordering the pool that’ll make you wonder if you’re still in Portland. 

How much does it cost? 

Soaking in the Kennedy School Pool is one of the best cheap things to do in Portland, making it a fun activity for even budget travelers!

  • $8 per person 12 and up
  • $4 per child ages 3-11 
  • kids 2 and under are free*

Can I bring a baby or young child? 

McMenamin's Kennedy School Soaking Pool | Things to do in Portland, Oregon

Yes, this soaking pool is baby friendly!

When we visited, there were two other babies in the water, so we felt comfortable bringing our daughter in. She loved it! We chatted with 2 other groups who said they see babies there all the time.

Of course, it always comes down to what you feel comfortable with, but the water temperature should be fine.

Good to know: You’ll need to call in advance to make a reservation for a soaking time slot (this helps ensure it never gets too crowded). Weekends tend to get quite busy, so make sure you call a couple of weeks in advance if possible. 

McMenamin's Kennedy School Soaking Pool | Things to do in Portland, Oregon

More things to do at McMenamin’s Kennedy School

  • If you have time, explore the rest of the venue. You can still glimpse relics of what it used to be like. Scope out class pictures on the walls, and if you use your imagination, you’ll see that the public bathrooms have a bit of an “elementary” feel to them.
  • Go to a movie at the cool onsite theater (complete with comfy couches!).
  • Depending on how scholarly you’re feeling, there’s both a “detention” bar as well as an “honors” bar.
  • If you’re craving pizza, head to nearby Ranch PDX for some of the best deep dish we’ve ever had!

Fun to know: If you’re not from Oregon, you might be unfamiliar with McMenamins, so allow me to introduce you to this Oregon staple… This is a family-owned conglomerate of mostly historic buildings that have been converter into entertainment venues, pubs, craft beverage makers, and hotels, all with quirky vibes. Once you start looking, you’ll see the name McMenamins around the city (and state!) quite a bit. 

6. Explore the eclectic Mississippi Avenue neighborhood


With adorable shops, quirky bars and houses turned into trendy, restaurants serving sustainably-sourced food, Mississippi Avenue and its surrounding North Portland neighborhood has an eclectically charming vibe.

You could easily spend the day popping into different joints, sampling the local flavors and toasting to a great visit to Portland (craft beer in hand! But more on this later).

¿Por Qué No? Taqueria on Mississippi Ave.

Restaurants on Mississippi Ave

  • Por Que No Taqueria: This adorable house-turned-taqueria in the Mississippi neighborhood seems to always be packed – a sign that the food is more than just alright. Try their tacos or signature margaritas.
  • Mississippi Pizza: Neighborhood staple featuring wood-fired pizzas, live music and trivia.
  • Gravy: Hearty American-style brunch in a casual setting.

Drinks on Mississippi Ave

  • StormBreaker Brewing: If you’re looking for a top-notch craft beer, StormBreaker is a fun place to wet your whistle.
  • Prost: This German-style beer garden is also home to a food truck pod, making it a good stop for drinks and food.
    • They host trivia on Thursdays, and on Wednesday nights they have a burger and beer pairing for $15 (which they reveal on their Instagram stories).

Sweets on Mississippi Ave

Live Music on Mississippi Ave

  • Mississippi Studios: This restored church is a live music venue and serves food and drinks.
  • The 1905: Live jazz, artisan pizzas and craft cocktails in an intimate, speakeasy setting.

7. Taste the best donuts in Portland

Mikiko Mochi Donuts best donuts in Portland
Mikiko Mochi Donuts

(Spoiler Alert: It’s not where you expect!)

If you’re a doughnut fanatic, you’ll be pleased to know that Portland has a huge variety of shops that specialize in this tasty treat, and you should definitely sample one (or 5!) while in this city.

From the touristy “must visit” shop (Voodoo!) to local secrets (like Mikiko Mochi and Doe Donuts), we’ve eaten a lot of the supposed “best donuts in Portland” all in the name of “research”.

We have an entire guide to the best donuts in Portland where we spill which places are worth the hype (and which aren’t).

Really love doughnuts? If you’re really into these circular treats, you might want to do a doughnut tour, where you can sample bites from all the best shops in Portland.

8. Chase waterfalls in the Columbia River Valley


You don’t need to get far from the city to immerse yourself in nature. Just 25 miles east of Portland lies the Columbia River Gorge where you’ll find some of the best waterfalls near Portland, as well as a smattering of trails and forests.

Just be warned that unless you make an effort to ditch the crowds, you won’t find much solitude. In fact, near some of the more popular waterfalls like Multnomah, it can be difficult to find parking. 

Tip: If you plan to visit the gorge area, you’ll need a vehicle. If you don’t have your own, consider getting a rental car (which is actually pretty affordable), or you can book a tour, however, this means you can’t go at your own pace.

Below are a handful of the waterfalls in this area that are relatively easy to access:

Multnomah Falls


Just a 30-minute drive from Portland, this iconic beauty is the most popular waterfall in the area, but for good reason. It’s spectacular. Visiting Multnomah Falls is a must if you’re in the Columbia River Gorge, but expect crowds.

Note: We visited during a busy time of year, and there was a stop along the highway where you could park and take a shuttle for a $5 round trip. We passed this up, crossing our fingers that there would be a spot closer to the falls, and we got lucky!

Important: From July – September, timed reservation tickets are now required to visit Multnomah Falls between 9 a.m. and 6 p.m. daily. Visit Recreation.gov to reserve your tickets.

Horsetail Falls


This easily accessible waterfall is a popular place for visitors to cool off and swim in the pool beneath the falls.

Latourell Falls

The easy 2-mile loop to get to this towering waterfall is less trafficked than some of the others in the area. This is one place in the whole gorge where we had a sense of solitude and didn’t find any crowds.

Oneonta Gorge

Oneonta Gorge Trail near Portland Oregon

Though the trail is only about 1-mile round trip, it takes a bit of time, as you’ll be walking IN the river bed!

Trek through waist-deep water to get to Oneonta Falls, which is gorgeous, and take in the unique experience of walking in the river. This was our favorite stop in the area.

Tip: Make sure you’re wearing sturdy shoes, like Chacos!

Our advice: If you want to stay somewhere near the Columbia River Gorge, consider making a trip to nearby Hood River, where there are tons of things to do to keep you occupied for a weekend or a whole week!

9. Satisfy your ice cream cravings

I am an ice cream addict. It doesn’t matter how cold it is or how full I am.

My motto is “there’s always room for ice cream”. And thankfully, Portland agrees with my motto and is home to some seriously good ice cream shops.

Here are 2 Portland ice cream shops you should try:

Our personal favorite: Salt & Straw

  • 4 Portland locations

Similar to donuts, there seems to be an obsession with a local ice cream chain, Salt & Straw. They are known for unique flavors – like pear & blue cheese, olive oil and honey lavender – and a line that’s always out the door. (Well, that is, unless you visit on a chilly November day like we did. No line for us!)

Let’s just say that while Voodoo Donuts came in short compared to its hype (in our opinion!), Salt & Straw stacked up and met our (high) expectations, and then some.

We’ve been a few times and are always so impressed by their unique and gourmet-inspired flavors that are constantly changing with the seasons.

They also have some more traditional flavors too for less adventurous eaters and ice cream purists.

Insider Tip: If you want to try two flavors but don’t want a double scoop (saving those calories and cents!), they can split a single for you. Also, their waffle cones are excellent and make a worthy upgrade!

Best vegan ice cream: 50 Licks

  • 2 Portland locations
Portland Ice Cream 50 Licks

Vegan? Lactose-intolerant? Just trying to limit your dairy intake?

If you can’t eat traditional ice cream, you’ll love 50 Licks’ large selection of non-dairy scoops that we can attest taste like the real deal! (Thank goodness for creamy, creamy coconut milk!)

They also have traditional ice cream (aka with dairy) that’s hella good too. Yeah, I just used the word hella, and yes, it is well-deserved.

With inventive flavors like coconut lemon saffron, lavender salted caramel, mango sticky rice, horchata, and Oregon Blackberry (just to name a few!), you might have a hard time choosing.

Lucky for you (and us!) they have the option to get small scoops so you can sample a couple different flavors.

Pro Tip: Ben got 2 small scoops and so did I, so we were able to enjoy 4 different flavors. Heck yes!

Wanna get some steps in with your indulgences? Check out this walking ice cream tour of Portland. You’ll get to taste 12 different flavors as you make your way around the city on foot.

10. See what’s happening at Pioneer Courthouse Square

Pioneer Courthouse Square | Things to do in Portland

Nicknamed “Portland’s living room”, this urban park is a popular gathering space and often plays host to events or small festivals.

The amphitheater-style seating makes a nice place to rest your legs and people-watch. 

And if nothing else, stop at this square for Fried Egg I’m in Love’s famous breakfast sandwich (one of the best we’ve ever had!). There are a few other food trucks here, but it is well worth snagging a spot in line because it is one of those places that is worth the wait.

11. Visit Willamette Valley Wineries

Willamette Valley Wineries Oregon

Napa Valley is known worldwide for its wines, but Oregon’s Willamette Valley isn’t far away and produces some fantastic vino that rivals its southern neighbors. 

Good to know: It’s pronounced “will-AM-it” (rhymes with “damn it”). Now, you’ll sound like a real local.

The valley’s microclimate is a perfect place for grapes of many varieties to thrive. In fact, the Willamette Valley is one of a handful of places in the world where Pinot Noir grapes grow really well. In fact, this region plays host to an annual International Pinot Noir celebration each July.

Fun fact to impress your wine-o friends: the Willamette Valley is actually on the same latitude as Burgundy in France, which is known as the birthplace of Pinot Noir.

And don’t worry if Pinot Noir isn’t your cup of tea (err, glass of wine…?). If you’re not into the reds, the area is also known for its top notch Chardonnay and Pinot Gris, so you can still get your vino on!

For the ultimate wine-lover’s day trip from Portland, hop in your car and plug the town of McMinnville into your GPS. Simply drive the scenic roads between Newberg and McMinnville, and stop into any winery (there are many!) that piques your interest. 

Willamette Valley Vineyard recommendations 

Willamette Valley Wineries Oregon

We have only just scratched the surface of this region, but we’re sharing some of our favorites. (And we’ll keep updating this list as we have more time to drink wine in the name of “research”!)

We’d recommend making reservations as many of the vineyards book up in advance (especially during the summer).

Furioso Vineyard, just outside Dundee, is one Willamette Valley winery we really enjoy. We arrived mid-afternoon on a Sunday, and while all their tables were booked out for the rest of the day, we could purchase a bottle and sit on a secluded bench with a view of the vineyard (which we honestly preferred over a tasting table). There’s an upscale food truck that serves wood-fired pizzas and charcuterie boards if you need a nosh. 

More recommendations:

Important reminder: Be sure to have a designated driver if you plan to return to Portland in the evening. Or consider joining a winery tour. You’ll be shuttled around to some of the best wineries in Willamette Valley (without having to worry about having a DD).

Don’t want to make the drive? If you want a winery experience but don’t want to drive out of the city, head to Fullerton Wines for a tasting. They are super passionate and knowledgeable about wines, and their bottles are pretty reasonably priced.

Note: If you do the Lost Plate Food Tour (see #1 on this list), Fullerton Wines is the first stop. And damnnnnn, that charcuterie platter… #thisiswhatdreamsaremadeof

12. Relax with tea & traditional sweets at Lan Su Chinese Garden

Chinese Garden Portland Oregon
Chinese Garden Portland Oregon
Chinese Garden Portland Oregon
Chinese Garden Portland Oregon

We’d made many visits to Portland before we finally visited the Lan Su Garden, and I don’t know what took us so long!

Nestled in the center of Portland’s somewhat dodgy Chinatown neighborhood, this tranquil oasis feels a world away from the rest of the city. The perfectly manicured gardens take up an entire city block with their serene beauty. 

After wandering the paths around the gardens, head to the onsite teahouse and settle in with tea and traditional Chinese sweets to be truly transported.

Hours: open daily from 10 a.m. to 6 p.m. (closed on some holidays)


  • Adults: $14
  • Seniors (62+) / College students (with ID): $13 
  • Youth (6-18): $11 
  • Children (5 and under): Free

Looking for more Oregon adventures? We call the town of Bend home and thought it was about time to put together a giant guide to all the fun things to do in Bend, including where to eat, sleep and hang out.

13. Eat your way around one of the top pizza cities in the US

Best Pizza Portland, Oregon | Ranch PDX

Yes, you read that right: Portland has been named one of the best cities for pizza in the United States. 

This article even calls it “the best,” but I’m not going to go there as I don’t want to start an online war with my New York and Chicago friends. 

Wherever you stand on its ranking, there’s no arguing Portland has some pretty damn good pizza.

Best pizza in Portland

We can offer rave reviews (from personal experience!) for the drool-worthy deep dish pizza from Ranch PDX. With three eateries around the city, we visited the pocket-sized location in the Woodlawn neighborhood.

They serve full pies or “quarters” (around $8), which we thought were a really good size. And like their name implies, each order is served with homemade ranch. 

Our experience: Don’t hate, but I’m typically much more of a thin crust person and I don’t usually do the whole pizza-and-ranch thing… but hot damn. This place is delicious, and I’m itching to get back. We loved the “Number Four” (ricotta, sausage, chilis) and “Hawaiian” (bacon, pineapple, jalapeño).

Other Portland pizza staples

And if you’re into walking tours (we certainly are!), Portland even has a walking pizza tour you can join and experience Portland’s best pizza by the slice!

Looking for a post-pizza beer?

Keep reading for some of our favorite breweries in Portland…

14. Go brewery-hopping


Portland is known for beer for a good reason: The climate is perfect for growing hops.

In fact, Oregon is second only to the state of Washington in hops production. So it shouldn’t be all that surprising to learn that Portland is known as one of the best beer cities in the US!  

One of Ben’s high school friends, Jon, is a Portland brewer, and he showed us some of the best breweries in town on our first trip to Portland.

Whether you’re into IPAs, wheat ales, or you fancy nitro porters, you’ll find a brew to fall in love with because Portland has a seemingly endless amount of breweries. 

Just please don’t order a Coors Light…

The list below are some of our favorite breweries/taprooms we’ve visited in Portland; however, it is far from exhaustive. You’ll find a brewery on just about every block!

  • Stormbreaker Brewing: nice patio in the heart of Mississippi Ave
  • Lucky Labradorone of the oldest breweries in Portland, this has kind of a “dive” feeling (in a cool way), they use solar panels for their brewing (so cool!), they’re dog friendly (woof!), and they have darts (our favorite)!

Wanna try all the breweries but have limited time?

Consider joining a brewery tour! You’ll be shuttled around to some of Portland’s best breweries (without having to worry about having a DD) and you might even make some friends in the tour group along the way!

Hangover Cure: If you spent the previous night sampling Portland’s fantastic beer selections and wake up with a hangover (been there!), head straight to Pine State Biscuits. These hearty biscuit sandwiches are piled high with yummy hangover-curing goodness and are delicious even when you haven’t had a wild night. Try the mushroom gravy for a vegetarian option. Beware that this place is popular, so if you arrive after 10:30 a.m., you may find yourself waiting in line.

15. Take a Sustainable Farm Tour with Farm 2 Fork


By now you should already know that we’re really passionate about food. And over the years, we’ve become more and more interested in learning about where our food comes from.

So when we found out there is a new tour company, Farm 2 Fork Tours, that brings you to local sustainable farms and shows you how the food gets to your plate, we were stoked!

We couldn’t decide whether we’d rather see the seafood farmers on the Oregon Coast or dairy and vegetable farmers in the Willamette Valley… So we did both!

Easily two of the best day trips from Portland.

Here are some highlights from each tour:

Coastal Exploration Tour

Kelly's Brighton Marina Crabbing | Oregon Coast
Shucking Oysters on a ice tray
cooked Oregon crab
Fresh caught crab

Start Time: 10:00 am | Tour lasts 5-6 Hours 

  • Head to small fishing villages on Oregon’s Coast and see where lots of the local fish is caught and processed. You’ll even see how to filet a halibut (in the off chance that you ever catch one!).
  • Try your hand at crabbing! It’s pretty fun and you’ll likely catch some — though they do have to be male and over a certain size to keep. We caught quite a few but had to throw them all back in. But even if you’re not so lucky, you still get to eat an incredible crab lunch!
  • Learn how to shuck oysters and eat them to your heart’s content (with some white wine or beer, of course!)

Taste of the Willamette Valley Tour

Willamette Valley Tour

Start Time: 10:00 am | Tour lasts 5-6 Hours 

  • Begin at a local sustainable farm and learn how they raise animals and produce. Enjoy a beautiful lunch made completely with local ingredients in an idyllic garden setting. Oh, and pair it with local wine for the perfect touch.
  • Tour a working dairy farm and see what life is like for the cows. You can even try milking a cow before sampling a bunch of delicious cheeses and ice cream!
  • Tour a poultry farm where the chickens are truly well taken care of and allowed to roam free. Play with some resident pigs and learn about the sustainable practices that make this farm different than most. Then enjoyed a stunning hor d’oeuvres spread with local wines to round out the day!

If you’re interested in sustainability and food, we think you’ll really enjoy a tour with Farm 2 Fork. Not only do you get a day’s worth of incredible food, but you’re helping to support small farmers who are passionate about what they do and are operating with the environment in mind. 

Psst! As an added bonus, we’ve got a little discount code for ya! Discount Code: 2Wander for $5 off your tour!

Disclaimer: Farm 2 Fork invited us on these tours as a complimentary experience. As always, all opinions are our own.

16. Explore Portland by bicycle


Now that we’ve talked pizza and beer, let’s work off our indulgences on two wheels!

Portland is known as being a green city, so it’s no surprise that getting around by bike is a popular and easy mode of transportation. (It’s called “Biketown” for a reason!)

Not only is it an eco-friendly way for locals to commute to work, but it’s a great way to see the city as a visitor. Plus, you’ll get a little work out in!

Try Portland’s bike share program where you can rent a bike for $12.50 per day, or go on a guided bike tour where you’ll learn local secrets and stop at non-touristy parts of town.

Traveling to more than just Portland? Be sure to see this epic Oregon road trip itinerary handy!

17. Browse the iconic Powell’s City of Books

Powell's Books Portland Oregon

Powell’s City of Books is famous for being the largest independent bookstore in the world! And of course it’s located in Portland! 

Situated proudly on a major corner in Portland’s Pearl District, Powells boasts 9 rooms, 3,500 sections and nearly a million books. To say Powell’s is a book-lover’s dream is an understatement. 

Even though it’s a popular spot, we think you’ll be impressed by the endless rows of literature and that signature “bookstore smell”. And while this is no secret, it is still worth a stop whether it’s your first trip to Portland or your tenth.

Powell's Books Portland Oregon

The sheer number of books is mind-boggling, and the fact that they sell many second-hand titles makes our hearts flutter (these books get a second life!).

Insider Tip: Powell’s often hosts readings and book signings by popular authors, so check out their calendar of events.

18. Put your smarts to the test at Trivia Night

We’re huge fans of seeking out trivia or pub quizzes on our travels, as it’s a unique way to get a taste of the local nightlife scene wherever you are.

Are we good at trivia? Nope!

But it’s a fun night out on the town, and you can sometimes join other teams to make new (local) friends who can give you tips on the area.

There are tons of trivia nights scattered throughout Portland. See a full list here.

19. Taste spirits at a distillery


While we’re on the topic of booze, we can’t forget distilleries.

When it comes to alcohol, Portland does it all. In fact, Portland has the more female distillers than anywhere else in the world. Here are a couple to check out:

  • Freeland Spirits: Female-owned distillery with a really nice gin.
  • Eastside Distilling: Fun place to stop into and do a sample flight for just $5.
    • Our recommendation: We loved their Northwest-style gin (with only locally-sourced and foraged herbs and botanicals) and their cold press rum (made with coffee in place of water). In fact, we bought both of those to take home as a little Portland “souvenir”.

20. Nosh on finger foods at Abigail Hall’s High Tea

Abigail Hall High Tea | Things to do in Portland Oregon
Photo credit Abigail Hall PDX

After traveling around Scotland, we have fallen in love with the tradition of afternoon tea. Next time we’re in Portland, we’ll be making a reservation for high tea at Abigail Hall.

Hosted each Saturday and Sunday, this high tea is fun to do if you want to feel fancy-schmancy while enjoying finger foods and conversation. And tea, too, of course.

Oh, and if you want to take your tea to the next level, it’s worth noting that specialty tea-inspired cocktails are available too. 


21. Grab some grub at a food truck pod

Hawthorne Asylum Food Truck Pod

You won’t have to look hard to find food trucks in Portland.

Serving up everything from classic food truck bites to world cuisines, you’ll find a food truck that tickles your tastebuds.

If you want several options all in one place so you can do your due diligence of sampling as much food as possible, make your way to one of Portland’s many “food truck pods”. Yes, this is exactly what it sounds like: a gathering of trucks serving up tasty food! 

This means you can get street tacos, Guyanese curry, and Indian samosas all in one sitting.

Alder Food Truck Pod

Best food truck pods in Portland

  • Third Avenue Food Cart PodThis is one of the largest food truck pods in the city and has relocated from its Alder Street location to the south side of the North Blocks Park. But beware, many of these food trucks are only open for lunch, and some are closed on weekends. When we arrived in off-peak hours, there weren’t many stands to choose from.
  • CartopiaLate-night food truck pod favorite, you’ll find a selection of your comfort food favorites like pizza, crepes and wood-fired chicken.
  • Mississippi MarketplaceSituated next to the German beer garden Prost, you’re able to enjoy food from one of the trucks as long as you order a beer with which to wash it down!
  • Hawthorne AsylumOne of the most recently-opened food truck pods in the city, as the name implies, Hawthorne Asylum sits on what used to be the grounds of a mental hospital. But unlike the name implies, the food is far from creepy. There is an awning, a communal fireplace, and a covered area, making this a good choice to grab a bite any time of the year.
    • Our recommendation: We liked the chicken and potato curry from the Guyanese stand (Bake on the Run). The owner is very nice and was offering (multiple!) generous samples to passersby.
  • Pine Street Market: While not a food truck pod, this indoor food court gives you the variety that food trucks do without having to brave being outdoors on a rainy day.

22. Catch a soccer match

Thorns Soccer game Portland Oregon
Thanks to our good friend, Alex Sturtz, who lives in Portland for letting us use her photo of the Thorns (women’s soccer) game.

While Oregon doesn’t have an NFL team, sports fanatics can still catch a football game in Portland… but the other football.

The Portland Timbers (Major League Soccer) and the Portland Thorns (National Women’s Soccer League) are both well-loved teams and games are known for having a lively atmosphere.

Tickets are relatively inexpensive, making it a fun activity for both diehard fans and those who just want another fun activity to add to their Portland itinerary.

23. Picnic on Sauvie Island & find a hidden UFO


If the weather is particularly nice while you’re in Portland, consider making a little day trip to Sauvie Island.

Just 10 miles northwest of downtown Portland, this is one of the largest river islands in the United States and much of it is farmland and wildlife refuge, and it’s a truly a peaceful escape from the city.

There are so many things to do on the river island that you could spend an entire summer day exploring!

Things to do on Sauvie Island:

  • relax at the beach
  • go berry picking at one of the many farms
  • get out on the water in a kayak
  • explore the island by bicycle
  • feel completely free at the island’s clothing-optional Collins Beach
  • have a picnic and watch the sunset
  • find the secret UFO (directions below)

24. Find the Collins Beach UFO


Walk to the “UFO” on Collins Beach for an interesting sight. This saucer-like shipwreck is adorned in skillfully-done graffiti and is a colorful surprise in the middle of the thick bushes that line the beach.

Here is the location of the UFO.

Just a heads up: Collins Beach is a clothing-optional spot and the UFO is often a spot where people gather to smoke weed and party.

25. Get coffee, but make it weird

Coffee shops in Portland, Oregon

When it comes to beverages – beer, wine, spirits – Portland does it well. And coffee is no exception.

Portland is a city where you’ll want to avoid Starbucks or other big chains. There are just too many cute locally owned shops to pass them by.

Nearly every corner has a cute coffee shop, so you’ll have no trouble getting your caffeine fix before a day of exploring. 

But if you want to have a true Portland experience, seek out a weird coffee shop, like these…

Robot Baristas that make your coffee

Artly Cafe is unlike any other coffee shop you’ve been to. The baristas are not going to be a great at conversation because they are not human… Prepare to be mesmerized as a robot barista prepares the perfect cappuccino!

Quirky coffee shop with desserts & live music 

Rimsky-Korsakoffee feels like you’re stepping into someone’s house — a very eclectically-decorated house, I should say. With funky (and a little weird!) decor and cozy vibes, this isn’t an ordinary coffee shop. Some evenings there is live music, and they are known for their desserts — get the ginger cake or the raspberry fool!

Turkish coffee in a colorful double decker Bus

Tov Coffee & Tea is a colorful, funky cafe is situated in a bright red double decker bus that specializes in Egyptian and Turkish coffee. 

26. Visit the “Freaky But True” Museum

If you really want to experience the weirdness that is Portland, we assume this is the place to go.

We haven’t been, and I’m not sure I really want to… but it may be right up your alley.

Also, I should mention its real name is The Freakybutture Peculiarium and Museum… makes it all that much weirder, doesn’t it?!

Featuring what they proclaim to be “strange and creepy exhibits”, this museum is not recommended for children, as it is said to be “PG-13”.

Check out the Google reviews and website to see if this is a stop you want to put on your list. Some visitors claim the $10 admission ($7 on Tuesdays) is well worth it while others call it a “flop”. So if it sounds interesting, give it a go and decide for yourself. According to reviews, it should take just about 20 minutes to explore.

27. See the famous Portland Japanese Garden

Portland Japanese Gardens
Japanese Gardens in Portland
Japanese Gardens in Portland
Japanese Gardens in Portland

You probably wouldn’t expect to find exquisite traditional Japanese Gardens in Oregon, would you?

But strangely enough, Portland is home to what has been called “the best Japanese Gardens in the world outside Japan.”

We visited these gardens just a couple months after returning from Japan, so our expectations were high. The gardens are located in Washington Park and are truly stunning and made us wonder if we had been transported over the Pacific Ocean back to Japan!

Open year-round, these gardens are gorgeous during each season and make a nice morning or afternoon activity to escape the city and find Zen.

Hours: Wednesday – Monday, 10 a.m. – 6 p.m. (closed Tuesdays)

Cost: Tickets are $21.95 for adults

More information: A limited number of tickets are available for daily admission. Portland’s Japanese Gardens website has more information on hours and events.

28. Enjoy truly sustainable sushi

sustainable Sushi in Portland

Calling all sushi lovers… Portland is home to the world’s first certified sustainable sushi restaurant. 

Bamboo Sushi has been serving up conscious rolls since 2008 and now has 5 locations in and around Portland, as well as Seattle, Denver and the Bay Area.

If you want to get your fish fix while being kind to the planet, be sure to make a reservation, as this ultra-popular sushi joint books up.

29. Take in the iconic sights at Tom McCall Waterfront Park

Tim McCall Waterfront Park Portland Oregon

A narrow strip of green on the riverfront, this park is nice for a stroll, people watching, picnicking, or all of the above.

Here are some of the notable attractions in Tom McCall Waterfront Park:

  • Japanese American Historical Plaza: Located at the north end of the park, this area has cherry blossom trees, which bloom in the spring months.
  • White Stag Sign: When you get close to the Portland Saturday Market, look up and you’ll see the iconic White Stag Sign.
  • Mill Ends: If you cross the street near the south end of the park, you’ll see a median cap that looks like a potted plant. This is Mill Ends Park (described above).
  • Salmon Street Springs: A large water fountain on the south end of the park.

30. Visit an alpaca farm


The Marquam Hill Ranch is not too far outside of Portland, and is a fun stop to pair with some winery visits in the area.

You can pop into the shop if you’re looking to buy alpaca products, but the real attraction is the animals themselves.

You can arrange to go on a tour, or you can pay $5 to get up close and personal as you feed them. 

31. Get your geek on at a board game cafe


If you’re a board game nerd like us, Portland has the cure to all your geeky desires!

We liked Game Knight board game cafe for its cozy atmosphere, gigantic selection of games and a long list of craft beers (and cider)! 

Sadly they have since closed down, but luckily Portland has plenty of other board game cafes to choose from:

  • Mox Boarding House is a restaurant offering an extensive library of board games for check out or dining in.
  • Senet Game Bar located in southwest Portland offers up a full service bar and restaurant along with a library of board games to check out during your visit.
  • Guardian Games is more of a retail store, but they host in-house games and have a full service bar on site.

Alternative: If electronic games are more your style, head to Ground Kontrol for an arcade experience complete with a full-service bar, karaoke and DJs.

32. Tour the Pittock Mansion Museum (or just look at it)


Built in the early 1900’s by one of Portland’s most influential families at the time, this 23-room French Renaissance-style château can be visited on a tour.

The exterior of the mansion is sandstone, and the interior has been preserved to look as it did when Henry Pittock, a successful newspaper publisher, and his family moved into this spacious home in 1924.

Taking a tour of this historic home is one of the most popular Portland attractions, especially for first-time visitors. It can be easily paired on the same day you visit Washington Park, which has the Portland Japanese Gardens and the International Rose Garden.

The Pittock Mansion is open daily with limited ticket sales. Check the Pittock Mansion’s official website for open hours as they change seasonally.

Pittock Mansion Admission:

  • Adults: $1550
  • Seniors (65+): $13.50
  • Youth (ages 6–18): $11.50
  • Under 6: Free 

And like we said in the title, even if you don’t want to take a tour, there is still a reason to come and visit… The view behind the Pittock Mansion is one of the best in all of Portland. Check out #37 on this list for more details.

33. Find street art around the city 

Street Art | Things to do in Portland
Here With Love Street Art | Things to do in Portland

Portland, unsurprisingly, has a lot of street art.

Simply wander around the city and you’ll stumble upon a handful of murals, or use this Portland street art map to plan out a route.

Some neighborhoods have more than others, and if you’re really looking for a high concentration of street art, the Alberta Arts District is where you’ll want to go…

34. Take a fun class & support a local

Airbnb Experiences in Portland

Airbnb Experiences are a fun way to do something totally unique on your travels while getting to hang out with a local and support their passion. A win for everyone.

Since Airbnb Experiences are relatively new, some cities around the world don’t have much variety in their offerings. But let me tell you, Portland is not one of these cities. In fact, there are SO MANY highly-rated classes and experiences that it might be hard to choose.

For example: Have you ever wanted to learn how to make pottery?

Or what about stained glass?

Silver Rings?

Indigo-dyed wall hangings?

You can do all of those things while in Portland! #bestsouvenirever 

And if you’re not feeling crafty, there are other experiences too:

  • a class on canning and pickling
  • goat yoga
  • cooking class on an urban farm where you forage ingredients
  • bike trip
  • guided hikes
  • and lots, lots more!

If you have the time and want a super unique experience in Portland, you’ll find plenty of options on Airbnb Experiences.

Let us know which one you choose and how it was! We want to do one of these on our next trip to Portland!

35. Get lost in Forest Park


Portland is known for having lots of green space. But if you want to get away from it all and be immersed in nature without going far from the city, Forest Park is the perfect place to cure your nature cravings.

Located just northwest of downtown Portland, this 5,172-acre park is not only the biggest park in Portland (by far!), but it’s one of the largest urban forest reserves in the United States (the 3rd largest on the west coast).

With more than 70 miles of trails for running, biking or just exploring and lovely views overlooking Willamette River, Forest Park’s thick trees and winding paths will make you forget you’re still technically in the city!

So lace up those walking shoes, pack a picnic, and get lost in the woods.

36. Cheers with a view at a rooftop bar

If you happen to be in Portland on a sunny day (not as rare as you might think!), head to a rooftop bar for afternoon drinks, light bites and a view. 

Departure Lounge Rooftop Bar | Things to do in Portland Oregon
photo credit: Departure Lounge

Departure Restaurant + Lounge

The most famous Portland rooftop bar is undoubtedly the Departure Restaurant + Lounge. With two balconies — one for diners (make reservations) and one for those seeking cocktails and snacks (like sushi, steamed buns and oysters) — you can cheers with a view of the skyline and the Willamette River below. (Psst! Expect to pay $15-$20 per cocktail.)

Note: Departure is currently undergoing renovations. Check their website for information on reopening.

Google Maps

Tope Rooftop Bar | Things to do in Portland Oregon
photo credit: Tope


Perched atop the Hoxton Hotel, Tope is filled with two of my favorite things: plants & mezcal. The aesthetics are a vibe, as the kids say, and the small menu features staple Mexican dishes such as ceviche and tacos which are served with a view.

Google Maps

Noble Rot Rooftop Bar | Things to do in Portland Oregon
photo credit: Noble Rot

Noble Rot

With a tagline of “wine, booze, food, view”, Noble Rot is a 4th floor wine bar that features a menu that is constantly rotating with the seasons and highlights ingredients grown in their impressive rooftop garden.

It is recommended that you make a reservation.

Google Maps

Roof Deck at Revolution Hall | Things to do in Portland Oregon
photo credit: Revolution Hall

Roof Deck at Revolution Hall

This seasonally-open rooftop is everything you want on a beautiful day – epic views of Portland, string lights overhead, a buzzy atmosphere, and a variety of pub food and drinks!

Google Maps

37. See live music


We are huge fans of live music, and when we saw that an artist we like was going to be performing in Portland, it didn’t take much for us to buy tickets and start planning a trip. 

Live music is plentiful in Portland, from bars that have open mic nights, DJs or performers to the concert venues, you won’t have to look far to find tunes in this city. 

McMenamins Crystal Ballroom

This popular venue is really fun and has a spring-loaded floor so if everyone jumps at the same time the floor will bounce. Sounds weird, but it’s pretty cool!

They also have house-brewed beers and other beverages for sale. We really liked the size of this venue – not too big, not too small – Goldilocks style!

Google Maps


Fun Fact: A fun piece of Oregonian trivia is that you might see the name McMenamins around the city (and state!) quite a bit. This is a family-owned conglomerate of unique entertainment venues, pubs, craft beverage makers, and hotels.

Insider Tip: If you’re going to a show at McMenamins Crystal Ballroom, stop by Al’s Den before doors open to grab a cocktail and soak up the atmosphere. If you get there early try to get a seat down in the actual “den” where you can enjoy live music and comedy.

More live music venues in Portland

There are plenty of venues around the city, and many cafes and restaurants also host musicians occasionally, so you can quite literally stumble upon some live tunes. But if you want to plan in advance or see a major artist, here is a list of live music venues to start with.

38. See a movie in a quirky theater

Hollywood Theater Portland Oregon

Going to the movies is a perfect activity for a rainy day in Portland. But, like, not a normal movie theater. 

Because this is Portland we’re talking about, let’s get a little weird…

This city is home to quite a few quirky theaters, so you’ll have your pick of unique venues to choose from.

Hollywood Theater

This historic non-profit theater shows classic movies, second-run features, ​and foreign films.

Google Maps

Bagdad Theater & Pub

A McMenamin property, the architecture of this historic building is as much of an attraction as the shows. Enjoy a movie with pub fare and local brews.

Google Maps

Kennedy School Theater

Another McMenamins establishment, this cozy theater features couches instead of chairs and shows recently-released films for just $5 per ticket. Before your showing, take a dip in their warm outdoor soaking pool (see #6 on this list!) for a truly relaxing day.

Google Maps

Cinema 21

An artsy theater with more than 90 years of history, this is an excellent place to catch independent films and documentaries.

Google Maps

39. Laugh it up at a comedy show 

Get your giggle on for a guaranteed good time!

Portland has quite a few comedy clubs to choose from:

Check out what shows are going on during your travel dates and make reservations.

40. Do an escape room

Escape Room Bend Oregon
This is a photo from an Escape Room we did in our home town of Bend, but you can find similar experiences in most major cities.

We kind of love escape rooms! Are we good at them? Umm not really, but still, it’s such a fun and unique way to spend an afternoon or evening.

And there are weirdly a lot of escape rooms in Portland. I suppose they make a great rainy day activity if you find yourself in a Portland drizzle.

We think escape rooms are best with 3 – 6 people; however, you can usually have as many people as you’d like up to 8. Just keep in mind, too many people becomes chaotic, and too few is kind of difficult. (That said, we have done a couple of escape rooms just the two of us and had a good time!)

So if you’re traveling to Portland with friends and want a fun night, make reservations at one of these escape rooms:

Next time we’re in Portland, I guess we need to round up some friends so we can have a go at one of these!

41. Snap a pic of Portland’s 2 most iconic signs

There are all sorts of photo ops around Portland, but there are two popular shots most travelers snap.

“Keep Portland Weird” sign

Keep Portland Weird Sign | Things to do in Portland Oregon

This mural is situated at the back of a small public parking lot, and it’s one of the most photographed spots in the city.

While your pic will likely be photobombed by a smattering of parked cars, it’s still a fun shot!

It is located on Burnside Street directly across from the famous Voodoo Donuts.

This is the exact location of the “Keep Portland Weird” sign.

White Stag Sign

White Stag Sign | Things to do in Portland Oregon

This sign is a symbol of Portland and has quite the storied history. 

First appearing in 1940, this sign has changed ownership many times over the years. 

From a sugar brand to a sportswear company, the outline of the state and the white stag have stayed the same, but the words on the sign have changed with each new owner. Currently, it simply says “Portland, Oregon” in a vintage script.

Fun Fact: During the holiday season, the nose of the deer is lit up in red, a la Rudolph. This long standing tradition is a subtle nod to Christmas, and began in 1959.

Here is the location of the White Stag sign, right along the Tom McCall Waterfront Park.

42. Get the best view of Portland

Things to do in Portland Oregon | Skyline View Mount Hood

Just behind the Pittock Mansion is one of the best views in Portland.

This vantage point overlooks the city, and on a clear day, you’ll see Mount Hood looming in the distance. Come at sunset for a really impressive sight.

This is the exact location of the viewpoint.

43. Shop local at the Portland Saturday Market


Each Saturday from March through Christmas Eve, part of the Tom Mccall Waterfront Park turns into an open-air market where artisans and vendors can sell their wares.

Browse jewelry, pottery, photography and other goods.

And when your tummy starts a rumblin’, let your nose lead the way to steaming tamales, homemade quiche and freshly baked pastries.

Looking for Portland Farmers Markets?

If you’re on the hunt for locally-grown produce and a variety of artisanal vendors, you’ll be happy to know there are a variety of farmers markets in the Portland area to visit. Stock up on locally-grown produce (to cook up a meal at your Airbnb!) and explore the rows of vendors selling artisan goods.

Check out the different seasonal farmers markets in Portland and find one near your hotel.

Many are open seasonally, but the market on Portland State University Campus is open every Saturday year-round. 

Insider Tip: See if your trip to Portland coincides with the Night Market. This event takes place every couple of months and would be cool to check out if your dates line up!

44. Go to a secret concert

Portland Sofar Sounds

Are you a fan of live music and surprises?

If so, you’re gonna love this one…

Sofar Sounds curates concerts in unique and intimate settings. But here’s the catch: You won’t know who the artists are or where the show is at until a day before the show.

Here’s what you will know:

  • Each Sofar Sounds show features 3 different musicians of varying genres.
  • The show will be in a cool and intimate secret venue. Think a museum, a distillery, a rooftop, or even a private home.
  • The booking page will provide clues of what you can expect, like if it’s an outdoor show or located at a residential venue.
  • When you purchase a ticket, you’ll know the neighborhood and the date.
  • The location and artists will be revealed 36 hours before the show.

Sound like your idea of fun? (Personally, we think it’s such a cool idea!)

See the calendar of upcoming events and purchase tickets here.

45. Go on a scavenger hunt to find historic horse rings

Portland Oregon sidewalk horse ring

Throughout Portland’s historic neighborhoods, you can find metal rings on the edge of the sidewalks. These were once used to tie up horses when they were the primary mode of transportation.

When the city was going through modern construction in the 1970’s, they started to remove these rings only to be met with public outrage. Residents complained that they were taking away a part of history. The removal of them ceased, and there is now a law that if you build a new sidewalk, the original rings must be put back in place once the job is done.

It’s kind of fun to make it a mission to see how many horse rings you can spot!

In true Portland fashion, some people have tethered toy horses to some of these rings in a sort of “urban art installation”. 

46. Hang out with Mary Jane

If you want to partake in smoking (or eating!) cannabis while in Portland, you’ll be pleased to find many, many options. Recreational marijuana use is legal in Oregon (and neighboring Washington and California), and there are many dispensaries around the state. 

Type “dispensary” into Google Maps and you’ll see all the options around your location. Pop into one, ID in hand (at least 21 years old), and chat with the staff about what you’re looking for. They tend to be very helpful in getting the right product for you.

Legal note: By Oregon Law, you cannot consume or smoke weed out in public or in an automobile, even if it is parked. If you are just visiting Portland, your best bet would be to go to a private establishment where is it legal to consume or smoke cannabis.

Tip: Most dispensaries only accept cash, so be sure to have some money on hand.

47. Explore the Alberta Arts District


This neighborhood is situated north of the Mississippi neighborhood, and runs east to west. Known as the “arts district” it should come as no surprise that this is the best place in Portland to peep some street art!

Insider Tip: There is artwork everywhere, but one mural that is particularly beautiful is on the La Bonita building (a Mexican restaurant).

In addition to lots of murals, you’ll find cute coffee shops, cafes, boutiques, psychics and more. Our advice is to park on one end of NE Alberta Street and walk the length of the commercial area.

Insider Tip: If you’re visiting Portland during the summer, see if your trip lines up with the Last Thursday Art Walk. As the name implies, this event takes place during the last Thursdays of June, July and August, from 6 – 9 p.m. It’s a fun way to see lots of vendors and artists come together.

48. Experience Portland’s legendary nightlife

Portland Oregon nightlife | Things to do in Portland

If you’re looking for a fun night out on the town, there are lotsa options, folks.

And it really comes down to what kind of nightlife you’re looking for…

  • Quirky Atmosphere: Alibi Tiki Bar
    • Our Airbnb host said the drinks and food aren’t really all that noteworthy, but the atmosphere is truly memorable. Gotta get there next time we’re in Portland.
  • Drag Show: Darcelle XV
    • If you want a super fun night out, why not catch a performance at the venue with the longest-running Drag Show on the west coast! Darcelle, the venue’s namesake, was recognized in 2016 by the Guinness Book of World Records as the world’s oldest drag queen (85 years old at the time).
  • Jazz Club: The 1905
    • If you’re looking for a jazz club, you’ve found it! Come for some live music and craft cocktails!
  • Speakeasy Vibes: Al’s Den
    • We stopped here for a cocktail and snack (tater tots!) before our concert down the street at McMenamins Crystal Ballroom. The cozy atmosphere was almost reminiscent of a speakeasy, and if you get there early enough, you can snag a seat in the actual “den” where there are live music and comedy performances nightly.

49. Drive to the top of Mount Tabor

Mount Tabor Portland Oregon

Located in Southeast Portland, Mount Tabor is a forested park on top of a volcanic cinder cone with trails for walking and excellent views over town. 

Whether you’re looking to get some exercise or just scoping a view, this local favorite will feel like you’re outside the city without actually leaving Portland at all.

50. Visit Mill Ends Park (aka Smallest “Park” in the World)


In the case of this article, we didn’t save the best for last… in fact, we’d recommend you skip this popular Portland tourist attraction unless you happen to be very close by.

Not only is Mill Ends Park the smallest park in Portland, but it is the smallest in the world.

This 452-square inch “park” was dedicated in as a colony for leprechauns, serving as an example of Portland’s famous weirdness.

But don’t get too excited…

This is basically just a flower pot with a small tree, in the middle of an intersection, and we’d categorize it as a full fledged tourist trap.

This tiny urban park is not worth going out of your way to see. But if you’re in the neighborhood, it is fun to say you’ve stepped foot in… err, seen (you can’t actually step in it!)… the World’s Smallest Park and tick it off your Portland bucket list.

But seriously, don’t go out of your way.

How many days do you need in Portland?

Things to do in Portland Oregon | Skyline View Mount Hood

The ideal amount of time to stay for a visit to Portland depends on your interests, the activities you want to engage in, and whether you’re looking to explore the city itself or venture into the surrounding areas.

Here is our general guide to planning your trip duration:

  • 2-3 days: If you’re primarily interested in exploring Portland’s city life, its diverse neighborhoods, food scene, and cultural attractions, a stay of 2 to 3 days is often sufficient. This allows you time to visit popular spots like Powell’s City of Books, the International Rose Test Garden, and the Portland Art Museum.
  • 5-7 days: If you also want to explore the natural beauty surrounding Portland, including the Columbia River Gorge, Mount Hood, or the Oregon Coast, you might want to allocate additional days. Outdoor enthusiasts might find a week or more beneficial to fully appreciate the hiking, waterfalls, and scenic drives in the region.

Tip: Consider the timing of your visit. If there are specific events or festivals you want to attend, plan accordingly and adjust your stay duration.

Ultimately, the perfect length of stay varies from person to person based on individual preferences. Whether you’re drawn to the urban experience, outdoor adventures, or a mix of both. There are so many fun things to do in Portland, you could easily come back time and time again (like us!) and not get bored.

Where to Eat in Portland


Portland has a never-ending variety of very, very good restaurants. With so much competition, establishments need to be really high quality to keep up, or do something so unique that they stand out from the crowded restaurant space.

Portland restaurants have a huge culture of focusing on locally-sourced produce, and you won’t have to look far to find healthy or vegan options. There is also quite a variety of cuisines from around the world. Portland really is a foodie paradise.

There would be no way for us to make a truly comprehensive list of restaurants in Portland, as new ones are popping up all the time. However, we made a list of some that we have enjoyed or people have recommended to us. Just tryin’ to spread the love!

Our top Portland restaurant picks:

These are our favorite restaurants in Portland (so far!). Try them and let us know what you think!

Lardo Restaurant Portland Oregon
Lardo Restaurant
  • Luc Lac Vietnamese Kitchen: amazing Vietnamese dishes and fun cocktails in a lively atmosphere (one of our top Portland food recs!)
  • Fried Egg I’m in Love: Popular food truck with one of the best breakfast sandwiches we’ve had! (Expect a wait!)
  • Bake on the Run: Guyanese cuisine in a food truck in the Hawthorne Asylum pod. The owner is super friendly and offers free samples.
  • Pine State Biscuits: hearty breakfast sandwiches (good for hangovers!)
  • Oven and Shaker: excellent wood-fired pizza and cocktails
  • Bamboo Sushi: sustainably sourced sushi for the win!
  • Grassa: unassuming Italian place with handmade pasta in a quick and casual atmosphere
  • Boke Bowl: inventive bao buns, ramen, and other Asian fusion
  • Por Que No: street tacos, other Mexican fare, margaritas & a fun atmosphere in the Mississippi neighborhood
  • Ranch PDX: Best deep dish pizza we’ve ever had; there are a few locations in the city
  • Family Cafe: Located in Beaverton (a suburb southwest of Portland), this tiny cafe serves Arabic specialties like lamb shank over rice and Turkish coffee. The owners are from Afghanistan and are super sweet and the food is great, making this a good stop if you’re coming through the area.

More Portland restaurants:

These places are still on our list!

Favorite Travel Tip: Whenever we hear restaurant recommendations for places we’re traveling, we pin them on our Google Maps. That way, when we are looking for a place to eat, we can open our map and see what is near us. It also is a good way to look up reviews for places you walk past.

Travel Hacks E-Book

Portland Map: Our favorite spots!

Have you been wishing you could see all these places in one place?

Your wish is my command.


Now you’ve got your very own Portland map with all the top attractions and local secrets.

We’ve pinned each of our favorite things to do in Portland and have marked them with different icons so you can easily tell them apart. You’ll find top restaurants, activities, and landmarks on this Portland map.

Feel free to download it for easy access during your trip, or keep this article handy so you can find all these places in Portland!

Perfect Portland itineraries

Keep Portland Weird Mural | Things to do in Portland Oregon

There are so many things to do in Portland for every type of traveler. But with so much to do, it can be a bit overwhelming trying to plan your time. 

We decided to give you a little head start and create the perfect Portland itinerary for each type of traveler. You’re welcome!

Foodie Experiences in Portland

Portland is consistently ranked as one of the top food cities in America and for good reason! Below we’re sharing all of the best foodie things to do (including some can’t-miss drinks to try as well!).

  • Portland Food Tour
  • Willamette Wineries
  • Sample Portland’s best doughnuts or ice cream (or both!)
  • Go on a “Farm 2 Fork” tour
  • Go brewery hopping
  • Sample world cuisines at a food truck pod
  • Sample Portland’s best pizza

Best free things to do in Portland 

If you’re a budget traveler, we’ve got all sorts of free things to fill your time in Portland.

  • International Rose Test Garden
  • Forest Park
  • Explore the Alberta Arts District and Mississippi Ave neighborhoods
  • Spot street art
  • Get the best view of Portland
  • Mount Tabor
  • Shop at a Portland Farmer’s Market

First time in Portland

If you’re planning your very first trip to Portland, Oregon, these are some of the top sights to include on your trip.

  • Portland Japanese Gardens
  • Columbia River Gorge waterfalls
  • Pittock Mansion
  • Powells City of Books
  • Sample Portland’s best doughnuts
  • Food Truck Pod
  • Portland Farmer’s Market
  • Portland food tour
  • Best view of Portland

Outdoor Adventures in Portland

If you’re a nature lover, these experiences should be top of your list.

  • Forest Park
  • Columbia River Gorge waterfalls
  • Explore the city on a bike
  • Hike to the Witch’s Castle
  • Day trip to Sauvie Island

Rainy Day Activities

If you happen to be in Portland on one of the notoriously drizzly days, fret not – there are plenty of rainy-day activities!

  • Quirky movie theaters
  • Comedy club
  • Powell’s Books
  • Live music
  • Escape moom
  • Board game cafe
  • Brewery hopping
  • Nightlife

TOP RECOMMENDATIONS: Our Personal Portland Favorites

If we had to choose our very favorite things in Portland, this list would be it! Spread them over a few days, and boom — you’ve got yourself the perfect weekend in Portland! 

  • Columbia River Gorge waterfalls (Oneta Gorge is one of our favorites in the area)
  • McMenamin’s Soaking Pool
  • Spanish Coffee at Huber’s Cafe
  • Tea at Lan Su Chinese Gardens
  • Japanese Gardens
  • Pip’s Doughnuts
  • Salt & Straw ice cream
  • Portland food tour
  • Explore the Alberta Arts District and Mississippi Ave neighborhoods
  • Powells City of Books
  • Brewery hopping
  • Hike to the Witch’s Castle
  • Willamette Wineries

Our favorite places to eat in Portland:

Day Trips from Portland

If you’re looking to combine your trip to Portland with a few other places, or you’re a Portland local in search of nearby adventures, you’ve got a ton of options.

There are so many places near Portland that you can go for a quick adventure or a weekend getaway, that we decided to do an entire round-up of our favorite Portland day trips.

But if you’re looking for a few quick recommendations, here’s are 3 of our favorite Portland day trips:

Hood River Oregon Panorama Viewpoint | Portland Day Trips

Hood River

Hood River is just an hour away and has a charming downtown. There are some incredible wineries and fruit orchards just outside of town, and many excellent hikes nearby.

Astoria Oregon viewpoint | Portland day trips


This cute town is situated on the mouth of the Columbia River and is known for excellent seafood, a storied history, and as the backdrop for many films like Free Willy and The Goonies, among others.

Silver Falls State Park Oregon | Portland day trip

Silver Fall State Park

If you’re craving an outdoor adventure, Silver Falls is incredible. While it’s pretty well-known among Oregonians, many out-of-towners miss this gem featuring 10 waterfalls.

Where to Stay in Portland

Portland Oregon

First things first: You’ve gotta decide which neighborhood you’d like to stay in. And there are a lot to choose from, each with its own distinct personality.

The best choice is going to vary from person to person based on your interests, itinerary, and whether or not you have a car.

Best Portland neighborhoods

  • Pearl District: Ideal if you don’t have a car, this neighborhood is north of downtown Portland (and has a better atmosphere).
  • Northwest District: A bit more residential, this neighborhood isn’t far from the Pearl District, and there are lots of great options for eating.
  • Mississippi Neighborhood: Our personal favorite place to stay, this neighborhood is eclectic and fun. With lots of breweries and restaurants, you certainly won’t go hungry (or thirsty!) here.
  • Alberta Arts District: This neighborhood is quirky and fun with lots of boutiques and cute cafes. It’s a bit further from some of the city’s main attractions, so it would be convenient to have a car if you are staying here.
  • Central Eastside: Just beside the river, this is perhaps the best of both worlds. Near downtown, but more of a “neighborhood vibe”.

Portland Airbnbs

Portland has a number of cute boutique hotels and affordable Airbnb properties to choose from. We’d recommend browsing for your dates and preferred neighborhood.

Here are a few Airbnbs where we’d love to book a weekend:


Pink House off Mississippi Ave: Here’s your chance to stay in a quirky tiny home with what we think may just be the best possible location in Portland. Self-check into this modern small house that is steps away from restaurants and bars. We would love to stay here next time.

Portland Tiny House

Portland Tiny House (Alberta Arts): Featured in Airbnb Magazine, this light and open tiny house is hosted by kind and responsive owners. Access to unique amenities like a local pool and movie theater.

Good to know: Here are the city regulations for rental properties in Portland.

Bonus! We have loads of info on how to book Airbnbs, red flags to watch out for when booking, and our favorite Airbnbs in our Airbnb article.

Portland Hotels

Prefer hotels? There are several great hotels in Portland, ranging in price, location and amenities to suit your travel style.


High-End/Luxury Hotel: Sentinel, a Provenance Hotel – The best that Portland has to offer! Right in the heart of the city center, this classic exterior yet modern design, 5-star hotel has all the bells and whistles to make your stay in Portland fantastic. Perfect for the business convention traveler or a honeymoon couple.


Mid-Range/Couple Stay: The Inn at Northrup Station – Keeping it weird in Portland, this quirky hotel colorful, cute and perfect for any couple stay. It’s smack dab in the middle of Nob Hill Alphabet district, so you know it’s walking distance to everything.

Mark Spencer Hotel | Where to stay in Portland

Good value in the Pearl District: Mark Spencer Hotel – Ideally-located for a first-time visitor in the vibrant Pearl district, this boutique hotel is a great value. We stayed here on one visit to Portland, and while it’s not anything super special, it was one of the most affordable options in the area (especially when it comes to parking, which can be very expensive!). Plus, the staff was very nice and the location made a great base for exploring.

Portland FAQs

We get tons of emails with questions about traveling in Portland, so we thought we’d do our best to answer the most frequently asked questions right here.

Is Portland safe?

Portland Oregon safety

The media has recently been making Portland seem like it has become very unsafe over the last few years, after the 2020 riots. We’ve received countless emails and messages asking the same question:

“Is Portland a safe place to visit right now?”

In our opinion, the media has some things a bit out of proportion. 

Like any major city in the world, there are areas that are a bit dodgy. You probably don’t want to leave valuables inside your car (but I wouldn’t recommend doing that in any city). 

And there is a very noticeable population of houseless people in Portland; however, this has been true long before 2020.

We have visited Portland many times before and after 2020, and we personally haven’t felt too much of a long lasting difference in terms of safety.

That said, this is coming from our personal experience, and everyone will have differing perspectives and opinions about what they are comfortable with.

We can’t tell you definitively if you will feel safe in Portland, but hopefully our experience will help you know a little more about what to expect.

What is the best time of year to visit Portland?

Though Portland is a year-round destination, there are a few factors you should consider when planning your trip. 

The rainy season across much of Oregon runs from November through March. High season is during the summer months, when the weather is at its peak for outdoor activities and school holidays allow for family travel. 

The best time to visit Portland is from June through August when you have the best chance for warm, sunny weather, making this the perfect time to visit if you want to spend a lot of time outdoors. During the summer months, Portland also plays host to a variety of festivals and events.

We’re also big fans of traveling to Portland during May (when flowers are starting to bloom) and September, as it is less busy than the summer months.  

Which is the best Portland neighborhood to stay in?

The answer to this will vary depending on your personal travel style. Here are some of our thoughts…

Our recommendation: 

  • For first time visitors, the Pearl District is well-located near lots of attractions. 
  • For those seeking a cool neighborhood vibe, Mississippi is a good choice. 
  • And for those who want something in between, Central Eastside is a good choice.

What’s the best way to get around Portland?

Portland Oregon Tram

While having a car of your own or a rental car is nice (but be prepared for that parallel street parking!), the public transportation system in Portland is actually very convenient.

Good to know: If you are staying in a hotel downtown, there will likely be a pretty large fee for using the parking garage (which you will definitely want to do). Be sure you factor in this cost.

You can buy a 1-day pass for just $5, which will give you access to the metro, streetcars and buses. You can buy the pass at most kiosks at major stops. You’ll still have to do a little walking, but the city is pretty well-connected.

Ride sharing apps like Uber or Lyft are also an option if you have a larger budget.

If you stay in the Pearl District (or the surrounding area), many things are within walking distance.

Where else should I go on my trip to Oregon?

Being that Oregon is our home state, we have TONS of content to help you plan your trip. Start with our Oregon Homepage and be sure to check out the articles below. Leave us a comment if you have any more questions!

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Are you planning a PNW trip?

You’ll definitely want to check out these articles for elsewhere in the PNW to help you plan your trip!

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Things to do in Portland Oregon | Two Wandering Soles
Things to do in Portland Oregon | Two Wandering Soles

We want to hear from you!

Which of these weirdly awesome things to do in Portland is going to straight to the top of your bucket list? Is there anything you think we missed? We’d love to hear from you in the comments below!

Comments (46) on “50 Weirdly Awesome Things to Do in Portland, Oregon

  1. Jyoti says:

    Thank you for including all the details. Your above information will definitely helpful for all the travelers. I really enjoyed your post. You include all the points and I really agree with them.

  2. ilan says:

    I find myself ensconced within the realms of your blog, where intellectual exploration unfolds like an enchanting ballet, with each pirouette of thought and cadaence of expression enthralling the mind and stirring the depths of the intellect.

  3. Bwindi F. says:

    Thanks for sharing such a diverse range of activities and tips. I’m excited to explore Forest Park and indulge in the local food scene. Your personal touch makes this article feel like a friend’s recommendation. Can’t wait to use this guide for my upcoming trip!

  4. Ginny says:

    Planning our first trip to PNW Portland this summer! Love that I came across your site in my search of things to do as it increased our excitement to visit! I am bookmarking many of your suggestions! My husband does have some disabilities so I will be researching more closely the state parks/waterfalls, etc as we love nature scenery but need to ensure not to strenous of hikes for him. We definitely are foodies and enjoy our wine so love the “tips” for food and wineries provided. We become overwhelmed with too many food choices so helpful to have and appreciate the more local population recommendations! We live in tourist area of Clearwater, FL so when we travel, we look for more what locals like as we understand the “tourist trap” phenomenon! And, as a side note, we have Voodoo Donuts at City Walk in Orlando, not a huge fan either so we will be bypassing this on our Portland trip. But will be visiting your replacement recommendations! Thank you

    • Ben Zweber says:

      Hi Ginny,
      We hope you have the best time in Portland and the surrounding area! I think we are on the same page about Voodoo Donuts 😉 There are so many great donut options in Portland!

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