50 Things To Do in Wonderfully Weird Portland

50 Things To Do in Wonderfully Weird Portland

The Ultimate Portland Bucket List. Top 50 things to do in Portland including popular tourist attractions, unusual things to do, best food and drink establishments, and day trip idea's from Portland!

Portland is a hip and easy town to spend a few days in. Getting around is no problem because of the great public transport infrastructure and because the whole downtown area is small enough to cover on foot if you really want to. There are many mouth-watering restaurants and food pods to explore, unusual activities to try, and even outdoor recreation nearby if you're feeling inclined. Here is the ULTIMATE Portland Bucket List for your trip!


Portland Bucket List - 50 Top Things To Do Unique To This Wonderfully Weird City


Tourist Attractions in Portland

1. St Johns Bridge

St Johns Bridge is iconic to Portland and structurally the most beautiful suspension bridge ever built. Spend some time strolling Cathedral Park underneath and viewing the Gothic arches of the bridge from below.

2. Pittock Mansion

Built in 1914, the Pittock Mansion tells the story of Portland’s transformation from pioneer town to modern industrialized city through the history and legacy of one its most influential families, the Pittocks. You can take guided or self-guided tours which are included in with general admission tickets.

3. Portland Aerial Tram

For some great views of downtown Portland, the Williamette River and even Mt Hood, jump on the Portland Aerial tram! The cabins depart approximately every five minutes usually taking about four minutes travel time each way. You can grab tickets at the tram terminal or check Groupon for combined Portland Tour plus Aerial Tram tickets which usually go for about $25 on their website.

4. Washington Park

What other city do you know of that has a forest smack bang in the middle of the city? Where you can be shopping downtown one minute and then strolling through stands of Ponderosa Pines and groves of Redwoods the next? Portland! Washington Park boasts miles of hiking trails and good views of Mt Hood on a clear day.

Portland Bucket List

5. International Rose Test Garden

It’s not called the ‘city of roses’ for nothing! Portland’s climate is perfect for growing roses. The International Rose Garden is home to over 8,000 rose plants with roughly 500 different varieties. It is a really beautiful place to be when the roses are in bloom. The best times to visit are between May and October although peak blooming happens usually in June.  

Portland Bucket List

6. The Japanese Garden

The Japanese Garden is nestled in the hills of Portland’s iconic Washington Park overlooking the city and providing a tranquil, urban oasis for locals and travelers alike. It encompasses 12 acres with eight separate garden styles including an authentic Japanese Tea House, meandering streams, intimate walkways, and a spectacular view of Mt. Hood.

7. Portland Zoo

Located in Washington Park near downtown Portland, the zoo can be accessed by train, bus, or even on foot. The zoo host’s concerts in the summer and ZooLights during Christmas.

8. World Forestry Center

The World Forestry Center has a variety of explorative exhibits featuring different types of forests from around the world, their unique characteristics and also sustainability challenges.

9. Portland Stag Sign

10. The Grotto

The Grotto is a Catholic Sanctuary set among 62 acres of botanical gardens containing beautiful statues and ponds. It is particularly beautiful in December when they hold their annual Festival of Lights event for Christmas. The spectacular event features concerts, outdoor caroling and other family entertainment but the biggest attraction is the quarter mile long trail displaying over a half million holiday lights.

11. Keep Portland Weird Sign

12. Tom McCall Waterfront Park in Cherry Blossom Season


Unusual Things To Do in Portland

13. Stark’s Vacuum Museum

Tucked away in the corner of Stark’s Vacuum Cleaner store is a collection of ancient vacuum cleaners where you can see how far we have come in vacuum cleaner technology. There are more than 300 types of vacuum cleaners displayed here.

14. Visit the Freakybuttrue Peculiarium

It doesn’t get any weirder than the Freakybuttrue Peculiarium. An odd museum that showcases strange exhibits like a nightmare dollhouse, fake crime scenes, pop artifacts and creepy fake severed body parts.

15. See a Roller Derby Game

16. Shanghai Tunnels

Portland was once known as the Forbidden City for it’s illegal practice of shanghaiing. Taking a trip to the Shanghai Tunnels might help to explain why. Portland’s underground consists of tunnels linking Old Town to the central area of downtown and the waterfront which were used to smuggle illegal goods including humans and conduct other illicit activities. You can explore these tunnels on the Portland Underground Walking Tour.

17. Naked Bike Ride

The Naked Bike Ride is an annual, clothing-optional event like you have never seen before. Imagine thousands of people casually riding past on their bicycles, with no clothes on. Well, you could be one of them… if you want. You would have to time your visit with the month of June.

18. Go on a Booze Cruise

Get boozey on the river with Portland’s Brew Barge. A brew barge, in case you did not know is a pedal-powered 14 person vessel. Cruising begins in April and runs throughout the summer.


Museums & Art in Portland

19. OMSI

20. Portland Art Museum

21. Take an Art Walk

On the first Thursday of each month you can participate in the Art Walk for an evening of art, wine and music. Many art galleries in the Pearl District and Old Town open their doors for free viewings and sometimes complimentary beer and wine. See their website for more information.


Food & Drinks in Portland

22. Spirit Tasting at a Distillery

Love your hard liqour? Then take a trip to Distillery Row where twelve independent distilleries produce everything from gin to rum, whiskey’s and other uniquely flavored spirits. You can find these locally handcrafted drinking holes in the Southeast and Northwest districts of Portland.

23. Sample Flights at a Brewery

Portland may very well be the Craft Beer Capital of the World with over 60 breweries in town! You simply must stop in at least one local brewery and sample some of the magic created here. Brewmaster’s in Portland add copious amounts of hops to create IPA’s that include flavors reminiscent of everything from pine to grapefruit. But don’t worry if IPA’s aren’t your thing, the breweries here have all the bases covered including lagers and sours too.

For fun: Join a guided brewery bicycle tour.

24. Stumptown Coffee Roasters

Stumptown got their start in 1999 and has been convincing their customers that they are the best coffee roaster’s in the nation since. I have to admit, I am not a huge fan of their coffee but that is because I prefer dark roast which they unfortunately do not serve. However, their Matcha latte’s are quite delightful.

25. Pine State Biscuits

26. Voodoo Donuts

Okay, so this donut shop constistanly makes everyone’s Portland Bucket List but many will tell you that they don’t actually taste as amazing as they look. I am going to say this is quite true although there are a few flavors I am partial too such as Grape Ape and the Pina Colada. What they lack in taste they make up for in their instagram-worthy appearance.

27. Doe Donuts

A much better tasting and lesser known donut store is Doe Donuts. They specialize in vegan donuts that are made from scratch using local ingredients. Doe offers year-round and unusual seasonal flavors. Be sure to find your way here, you won’t regret it.

28. Departure

This restaurant and bar makes it on the bucket list because of it’s incredible rooftop views of the city, river and mountains. Departure sits on top of the Nines Hotel in downtown Portland. Their menu consists of modern Asian cuisine and they boast the largest sake list in the city.

29. Salt & Straw

With flavors like Hibiscus with Rose Lemon Curd and Wildflower Honey with Ricotta Walnut Lace Cookies, you really would be missing out if you didn’t pay this ice cream store a visit.

Portland Bucket List

30. Tea Tasting at Smith Teamaker

If you enjoy sipping tea you need to pay Smith Teamaker’s a visit. Be sure to order a tea tasting which is basically just like ordering a flight of beer. You can choose four varieties from the menu including black and herbal tea’s.

31. Cartlandia

Portland is famous for its large number of food trucks found throughout the city and a trip to Portland would not be complete without a visit to one. Choose from a variety of trucks over at our favorite pod Cartlandia in the Southeast District.

32. Lardo

Lardo is a sandwich shop in Southeast Portland and while their burgers are superb, it is the fries you need to come and try. Known as the ‘dirty bastard’, the hand-cut fries are cooked in bacon fat then tossed with fried herbs and Parmesan.

Portland Bucket List - Top Things To Do in Portland

33. Eat World Famous Wings at Pok Pok

Pok Pok is on every foodie’s Portland bucket list for their famous chicken wings but we recommend checking out their other store, Pok Pok Wing too.

34. Wasabi Sushi PDX

Who doesn’t like sushi? This place serves instagram-worthy sushi donuts, sushi burgers, and sushi b-ritto’s that are wrapped in spicy cheeto’s but you can also order poke bowls and ramen noodles too.

35. The People’s Pig

Killer barbecue and delicious cocktails make it one of our favorite places in Portland to grab lunch.


Shopping in Portland

36. Portland Saturday Market

I know it’s called the Portland Saturday Market but it is actually open on both Saturday’s and Sunday’s. The markets are located on the waterfront and host local arts and crafts stores along with a plethora of exotic food options.

37. House of Vintage

38. Buffalo Exchange

39. Powell’s Books

One of Portland’s most famous landmarks is the Powell’s City of Books. This place is literally a multi-level maze and you could quite actually spend a few good hours in here. Grab a coffee from the attached coffee shop and spend some time roaming. It’s a great way to spend a rainy day.


Nightlife in Portland

40. Watch A Movie At A Brew Cinema

Portlander’s love their beer so naturally there are cinema’s in the city that serve adult beverages. You can take your pick between Cinemagic, McMenamins, Academy Theater and Laurelhurst Theater.

41. See the Rocky Horror Picture Show

Over at the Clinton Street Theater they have been showing the Rocky Horror Picture Show going on 40 years. For a unique way to spend a night join the interactive crowd for a showing of one the longest running films in history. Doors open 11:30 pm every Saturday night and the show starts at midnight.

42. The Doug Fir

43. Crystal Ballroom

43. Hawthorne Theater

44. Helium Comedy Club

45. Hervey’s Comedy Club

46. Dante’s

All sorts of events take place at Dante’s such as karaoke night (although the talent here are on another professional level), live bands and burlesque shows.

47. Moda Center

Whether you’re into music or sports, you can check out the Events Calendar for the Moda Center and see if your favorite entertainer or sports team will be performing on your travel dates.


Day trips from Portland

49. Chase Waterfalls in the Columbia River Gorge

Take a day trip out to the Columbia River Gorge and see Oregon’s tallest waterfall Multnomah Falls and many other stunning waterfalls that are in the area. You can rent a vehicle and drive yourself out or join this popular Portland Sightseeing Tour which includes a trip to the Columbia River Gorge or just take the cheaper Columbia Gorge Tour option.

50. Visit a Winery

The Williamette Valley is home to over 250 wineries and has become one of the nation’s leading producers of cool climate varietals like Pinot Noir. Portland is the perfect starting point for exploring quiet back country roads through Oregon’s wine country with more than half of the state’s wineries located only 45 minutes away. Take in beautiful vistas of rolling hills and the Cascade Mountains on this Wine Tasting Tour through the Williamette Valley.



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Portland Activities & Tours

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Got any of your own suggestions to add to this Portland bucket list? We would love to hear them in the comments below!