45 Weirdly Awesome Things to Do in Portland, Oregon (+ map!)

From must-see sights to hidden gems, this is the ultimate list of things to do in Portland, Oregon. This frequently updated 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.

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!

Our experience in Portland

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!

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!

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). 

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!

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

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.

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!

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

3. See the famous Portland Japanese Garden

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.

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. 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).

6. Get coffee, but make it weird

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…

7. Taste the best donuts in Portland

(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).

Best Donuts in Portland (it’s NOT where you expect!)

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. Browse the iconic 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! 

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.

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.

9. See what’s happening at Pioneer Courthouse Square

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.

10. Grab some grub at a 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.

11. 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!

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!

12. 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 me. The city is home to some seriously good ice cream shops afterall.

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.

13. 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.

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

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. 

Can I bring a baby or young child? 

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.

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. 

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

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.

16. 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. 

Our Advice: 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.

Check out our guide to best waterfalls near Portland for more info and inspiration!

15 Scenic Waterfalls Near Portland, Oregon (+how to see them!)

Tip: 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!

17. 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. (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!

18. 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.

19. 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 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!

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.

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

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

21. 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.

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.

22. Get the best view of Portland

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.

23. Find street art around the city 

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…

24. Take a fun class & support a local

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!

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

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. 

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

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.

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 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.

27. 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: 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.

28. 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.

29. Enjoy truly sustainable sushi

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.

30. Visit Willamette Valley Wineries

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. 

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

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).

31. 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. 

32. 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. 

Best rooftop bars in Portland

• Departure Restaurant + Lounge: The most famous Portland rooftop bar 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.
• 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.
• 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.
• 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!

33. 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. 

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, or you can check out some of our favorites below.

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.

34. See a movie in a quirky theater

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.

Quirky Theaters in Portland

• Hollywood Theater: This historic non-profit theater shows classic movies, second-run features, ​and foreign films.
• 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.
• 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.
• Cinema 21: An artsy theater with more than 90 years of history, this is an excellent place to catch independent films and documentaries.

35. 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:

• Helium: big name performers
• Kickstand Comedy: non-profit comedy club
• Curious Comedy Theater: non-profit comedy club
• ComedySportz: interactive improv

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

36. Do an escape room

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:

• Hour to Midnight
• In Search of an Exit
• Mental Trap Escape Room
• Escape Games PDX
• Escapism
• MindTrix Escape Room

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!

37. Catch a soccer match

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.

38. 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

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

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.

39. 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”.

40. Experience Portland’s legendary nightlife

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.

41. Go to a secret concert

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.

42. 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!

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

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”. 

44. Drive to the top of Mount Tabor

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.

45. 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.

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Portland map: Our favorite spots!

Click on the map and enter your email to gain access to our custom Portland Map.

It’s filled with 100+ custom pins of everything on this list, plus our favorite eateries, day trips and more! We’d made personal notes for each pin and included many of our personal photos so you know exactly what to expect from each pinned location.

How to Spend 1 day in Portland

Wondering how to fit all these great recommendations into a single day? We did the legwork for you and came up with what we think is the perfect Portland itinerary for just one day. 

How to Spend One Day in Portland, Oregon (+ epic itinerary ideas)

First timer’s guide to Portland

If this is your first time visiting the City of Roses, you’ll want to read our First Timer’s guide which is packed with helpful information like how to get around and where to find the best eats. 

First Time in Portland: Everything You Need to Know

Where to Stay in Portland

In this guide we break down the best neighborhoods in Portland to find short term accommodation when visiting. Plus, we’ve included our top recommendations for hotels and Airbnbs.  

Where to Stay in Portland, Oregon: Neighborhood Guide + Hotels

Day trips from Portland

There are so many places near Portland that you can go for a quick adventure or a weekend getaway, so we decided to do an entire round-up of our favorite Portland day trips. This guide is packed full of insider tips for where to go when you want to get out of the city. 

15 Best Day Trips from Portland

Don’t miss your chance to grab our Portland map!

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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!