17 Weirdly Awesome Things to Do in Portland

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

Not only is 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 did!

If you are planning a trip to Oregon's biggest city, we've got you covered. We've put together a list of the best things to do in Portland – from the super quirky local secrets to can't-miss top attractions. This Portland travel guide is just what you need to start planning your trip!

1. Hike to the Witch's Castle

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 river bank, this crumbling structure has been taken over by the forest, with vines creeping up the structure.

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 (fun fact: 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 it's 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.

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 at NW 30th and Upshur.

2. Explore the Mississippi Neighborhood

With adorable shops, quirky bars and houses turned into trendy, restaurants serving sustainably-sourced food, this 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!).

Foodie Tip: If you're hungry in the Mississippi neighborhood, grab some tacos at 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.

3. Browse the famous Powell's City of Books

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

While this is no secret, it is still worth a stop on your first trip to Portland. With 9 rooms, 3,500 sections and nearly a million books, Powell's is seriously a book-lover's dream. And even though it's a popular spot, we think you'll be impressed by the endless rows of literature and that signature "bookstore smell".

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 authors, so check out their calendar of events.

But if you've been-there-done-that and you'd like to browse some books at smaller shops, check out this list of Portland's best bookstores for lesser-known options.

4. Taste Portland's Best Donuts (Hint: It's not where you expect!)

It seems like everyone who ventures to Portland has an Instagram pic of the famous Voodoo Donuts. Yep, we did too.

We were hungry and the line didn't seem *that* long, so we decided to see if these fried sweet things live up to the hype. We ended up ordering 3 different donuts to sample (enough to try a few flavors, but not too crazy!), and we took them to a patch of grass down by the river to do our taste test. 

We hate to say it, but we were not all that impressed. That didn't stop us from finishing our donuts (hey, no wasting donuts for us!), but we don't quite understand where the Voodoo hype comes from.

If you're in Portland and you wanna give Voodoo a chance, give it a shot! But if you want to know where the locals get donuts, keep reading.

The Local Donut Choice in Portland

We were told by many locals (who rolled their eyes when we told them we went to Voodoo) that actually, the place to go for donuts is Blue Star Donuts. If you have a chance to try it out, let us know what you think!

Traveling to more than just Portland? Read up on the Best Places to visit on an Oregon Road Trip

5. Satisfy your ice cream cravings

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.

After our not so wonderful experience with the hyped up Voodoo Donuts, we decided to skip the ultra popular ice cream shop and try one that a couple locals recommended instead: Ruby Jewel. The thing that makes this ice cream parlor out of the ordinary is their sundaes and hand-crafted ice cream sandwiches. With 3 Portland locations, it makes a great stop for any sweet tooth!

Our Recommendation: Everything on the menu looked divine, but we created our own combo that was pretty fantastic: ice cream sandwich with homemade snickerdoodle cookies, hazelnut ice cream, and dipped in dark chocolate fudge.

Note: We've heard that unlike Voodoo, Salt and Straw actually is actually worth the hype (if you don't mind standing in a long line). So if you have time in Portland, give it a try!

6. 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! There are a few board game cafes to choose from, but we liked Game Knight for its cozy atmosphere, gigantic selection of games and long list of $5 craft beers (and cider)!  

Located in an unassuming residential part of north Portland, this board game cafe serves pub food and reasonably priced drinks (cocktails, wine, beer & cider).

Hours: Open until midnight Thursday - Saturday, and 11 p.m. on weeknights, a few hours at Game Knight is a great way to spend a few hours in the afternoon, or game the night away! 

Nearby food: If you're a carnivore looking to get your meat fix after some intense board gaming, The People's Pig is nearby and sure to satisfy your cravings. Though we never actually ate here (we had just eaten when we walked past), the smells were enough to pique our interest. Directly behind the tiny restaurant is a garden from which most of their produce is grown and the reviews online speak for themselves.

7. Explore Portland by bicycle

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. 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.

8. Go chasing 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 a smattering of waterfalls, 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. 

That said, visiting this stunning region is well worth the journey and is a perfect addition to your time in Portland.

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

Tip: If you plan to visit the Columbia River Gorge, you'll need a rental car!

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 (pictured above) 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 $5 round trip. We passed this up, crossing our fingers that there would be a spot closer to the falls, and we got lucky!

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 Columbia River Gorge that we had a sense of solitude and didn't find any crowds.

Oneonta Gorge

Though the trail is only about 1 mile roundtrip, it takes a bit of time, as you'll be walking IN the river bed! Trek through waist-deep water to get to Oneata 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!

*Important Note: Be sure to look up current conditions of the trails in the Columbia River Gorge. After the forest fires of 2017, many trails are undergoing reconstruction and may be closed. Be sure to check and see if the trails you're interested are open before making the journey out there. This site from the Forest Service lists the status of all the trails in the Columbia River Gorge post-fire.

9. Make a toast at a local winery

Napa Valley is known worldwide for its wines, but Oregon's Colombia River Gorge is not far away and produces some fantastic vino that rivals its southern neighbors. The gorge's microclimate is a perfect place for grapes of many varieties to throve.

This article from Portland Monthly walks you through some of the best wineries in the region, some of the best have places for picnicking and regularly host live music. A perfect escape from the city!

10. Picnic on Sauvie Island

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.

Relax at the beach, go berry picking at one of the many farms, get out on the water in a kayak, or explore the island by bicycle. 

11. Visit the International Rose Test Garden

Who knew there were so many varieties of roses?! (We sure didn't!) 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 things to do in Portland, so depending on the time of year and day of the week, it can get quite crowded.

12. See the famous Japanese Gardens

You probably wouldn't expect to find exquisite traditional Japanese Gardens in Oregon, would you? But strangely enough, Portland is home to stunning gardens that will make you feel as if you've been transported over the Pacific Ocean. Open year round, these gardens are gorgeous during each season.

Cost: Tickets are $14.95 for adults.

More information: Portland's Japanese Gardens website has more information on hours and events.

13. Visit the city's biggest and smallest parks

Portland is well-known for lots of green space and one of the top dog-friendly cities in the USA. There are plenty of city parks to choose from, but if you want to get into nature and also have a unique "park" experience, we've got two parks to add to your list!

Portland's Biggest Park: Forest Park

If you want to escape the city without going far, Forest Park is the perfect place to cure your nature cravings. Just west of downtown Portland, this is one of the nation's largest urban forest reserves, and offers lovely views overlooking Willamette River. With trails for running, biking or just exploring, Forest Park's thick trees and winding paths will make you feel as if you're far from the city. 

Portland's Smallest Park: Mill Ends Park (aka Smallest "Park" in the World)

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.

Basically just a flower pot with a small tree, 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.

14. Tour the Pittock Mansion

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.

Take a tour of this historic home while visiting Portland. Check out the Pittock Mansion's official website for ticket prices and hours. 

15. Shop the Portland Farmer's Market

There are a variety of famers markets in the Portland area to visit -- from those open seasonally to markets that run year-round, you'll be sure to find at least one market to browse during your visit to Portland. Stock up on locally-grown produce and explore the rows of vendors selling artisan goods.

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

Check out the different seasonal famers markets in Portland or head to the market on Portland State University Campus that's open every Saturday year round. Or if crafts are more your thing, check out the Portland Saturday Market.

16. Grab some grub at a Food Truck Pod

In true hipster fashion, you won't have to look hard to find food trucks in Portland. Serving up everything from classic food truck bites like street tacos to Ethiopian specialties, you'll find a food truck that tickles your tastebuds.

And if you want several options all in one place so you can do your due diligence of sampling them all, make your way to one of Portland's "food truck pods". Yes, this is exactly what it sounds like. A gathering of trucks serving up tasty food! 

  • Alder Food Truck Pod: Conveniently located in the center of the city near Powell's Bookstore, this is one of the largest pods in the city. 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.

  • Cartopia: Late-night food truck pod favorite, you'll find a selection of your comfort food favorites like pizza, crepes and wood-fired chicken.

  • Mississippi Marketplace: Situated 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!

  • Cartlandia: More than 30 different carts serving up cuisines from all over the world!

More info: Read up on Portland's Food Truck Pods and their hours.

17. Go Brewery Hopping

Just like Seattle is known for coffee, Portland is known for beer. One of Ben's high school friends, Jon, is a Portland brewer, and he showed us some of the best breweries in town.

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. 

Some of our favorite breweries/taprooms we visited in Portland were Ecliptic Brewing and Stormbreaker Brewing.

Can't decide on just one brewery?

Bailey's Taproom has a mind-blowing 26 beers on tap, so you can try many of the local brews without having to hop around town. And if you're wondering if there is enough of your favorite beer still on tap, you can check their website and it will tell you how full the keg is. Genius!

If Bailey's is packed, walk across the street to Upper Lip, a lesser-known bar with a considerable drink menu.

Wanna try them all 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, head straight to Pine State Biscuits. These 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 during peak hours, you may find yourself waiting in line.

Where to Stay in Portland

Portland has a number of cute boutique hotels and affordable Airbnb properties to choose from. Here are some of our choices we’d stay at when we go back to Portland.

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.

Budget/Social Hotel: HI Portland Hawthorne District Hostel - Offering private and dorm rooms, this is a great place to meet other travelers from around the world. Free breakfast, free WiFi and a fully-equipped kitchen to make your own meals. The city center is 2 miles from hostel, bus there is a bus stop close by.

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We want to hear from you!

Have you been to Portland? What was your favorite experience? What did we miss? We'd love to hear from you in the comments below!