50 Things To Do In Wonderfully Weird Portland
This is the ULTIMATE Portland bucket list! We’ve listed the best 50 things to do in wonderfully weird Portland including popular tourist attractions, unusual things to do, best food and drink establishments, and day trip ideas from Portland!
Portland is one of our favorite cities to visit because there is so much to do, many mouth-watering restaurants and food pods to explore, unusual activities to try, and even outdoor recreation nearby if you're feeling inclined.
Best of all, nearly all of the city’s highlights are very near each other so it is easy to see and do a lot in terms of activities on a one or two day itinerary.
Without further ado, here is the ULTIMATE Portland Bucket List for your trip!
Portland Bucket List - 50 Top Things To Do Unique To This Wonderfully Weird City
TOP TOURIST ATTRACTIONS IN PORTLAND
1. St Johns Bridge
St Johns Bridge is iconic to Portland and structurally the most beautiful suspension bridge ever built. Pedestrians can walk across the bridge’s narrow sidewalk to get an up close view of the architecturally stunning towers of the bridge, while also enjoying spectacular views of the Willamette River.
Afterwards, head down to gorgeous Cathedral Park which is situated beneath the bridge to see the stunning Gothic arches that the bridge rests upon.
In the summer, Cathedral Park is a wonderful place to enjoy a picnic, and during the fall you’ll be able to witness colorful autumn leaves throughout the green space.
St Johns Bridge is located in the St Johns neighborhood in Northwest Portland which has a great selections of cafes, restaurants, pubs, and bars.
We recommend strolling the main street of this neighborhood and stopping to get lunch or a beer at one of the local establishments. Some of the local businesses that are a must visit include Tienda Santa Cruz, The Sparrow Bakery, and StormBreaker Brewing.
St Johns Bridge seen from Cathedral Park in Portland
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.
In 1853, Henry Pittock (1834-1919), at the age of nineteen, headed west on the Oregon Trail to seek his fortune. When he arrived in Portland, the city was a frontier ‘stumptown’, competing with Oregon City to become the major trade and industrial center for the region.
Through hard work and taking a few financial risks, Pittock managed to build an empire acquiring the local newspaper, mines, ranches, and other businesses.
In the early 1900s, Henry Pittock wanted to use his fortunes to build a ‘mansion on the hill’ on property that had panoramic views of Portland, and in 1912, construction on the Pittock Mansion began and by 1914, Henry and his wife had moved into the property. Unfortunately, the couple only lived in the mansion for four years before they died.
Today, the Pittock Mansion is an iconic landmark in Portland and very popular with tourists and Portlanders.
Visitors can explore the 16,000 foot French Renaissance style mansion and tour its twenty-three opulent rooms. Guided tours are included with general admission tickets.
The property has incredible views of Portland’s skyline, the Willamette River and the Cascade Mountains.
Portland Aerial Tram
For some great views of downtown Portland, the Willamette River and even Mount Hood, jump on the Portland Aerial tram!
The cabins depart approximately every five minutes usually taking about four minutes travel time each way.
Cabins feature expansive floor to ceiling windows so bring you camera and be prepared to snap a few photos as you travel high above the city.
The Portland Aerial Tram connects the city’s South Waterfront neighborhood and the Marquam Hill neighborhood. It is one of only two commuter aerial tramways in the United States.
You can grab tickets at the tram terminal which cost $5.65 for a return trip.
4. Washington Park
View of Mount Hood seen from 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 is a 458 acre forested area situated within walking distance of downtown. The park boasts miles of hiking trails and terrific views of Mount Hood on a clear day.
5. International Rose Test Garden
Portland has been obsessed with roses since the late 1800s and at one stage in the city’s history, Portland had twenty miles of rose-lined streets. It was then that the city earned its nickname ‘City of Roses’.
The International Rose Test Garden was planted in 1917 and is now the oldest continuously operating rose garden in the United States.
At the Rose Test Garden are over 10,000 rose bushes which are typically in bloom from May through October although peak season is June.
This popular tourist attraction is located in Washington Park. The grounds are open every day of the week from 5am to 10pm. Admission is free!
The Portland Japanese Garden, which is nestled in the hills of Portland’s iconic Washington Park, provides a tranquil urban oasis for locals and tourists alike.
It encompasses twelve acres with eight separate garden styles and also includes meandering streams, intimate walkways, and an authentic Japanese Tea House.
At the gardens, visitors can immerse themselves in traditional Japanese arts in the Cultural Village through performances and seasonal activities such as learning about chado (The Way of Tea) during a tea demonstration, or watching demonstrations on the delicate art of flower arranging.
7. Portland Zoo
Portland Zoo is a great place to visit if you are traveling with kids. The 64 acres park is home to African, Asian, and North American animals including elephants, rhinos, and even a polar bear!
The zoo hosts concerts in the summer and other special events such as Zoo Lights during the Christmas holidays. Be sure to check their calendar for upcoming events and activities.
Portland Zoo is located in Washington Park and can be accessed from downtown by train, bus, and on foot.
Photo by Travel Portland
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.
Visitors can appreciate stunning Northwest regional architecture, watch documentary films in the theater, or explore society’s connection to forests through a variety of displays.
The center is located in Portland’s stunning Washington Park.
9. Portland Stag Sign
The Portland Stag Sign is an iconic Portland landmark and one of the most instantly recognizable parts of the Portland skyline.
Originally constructed in 1940, the sign has carried different messages advertising Portland companies but the longest lasting was for the White Stag Sportswear brand which is why this sign is often referred to as the ‘Stag Sign’.
The sign which is lit up every night, can be found on Burnside Street in downtown Portland near the Old Town Historic District.
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
The ‘Keep Portland Weird’ mural is an iconic spot in Portland and a popular destination with travelers looking for cool photo opportunities.
If you visit Portland, you need to get the obligatory shot in front of this famous wall. It is a must for all first time visitors!
The mural is painted on a wall behind Dante’s nightclub in downtown directly across the road from Voodoo Doughnut.
12. Tom McCall Waterfront Park in Cherry Blossom Season
If you’re planning on visiting Portland in spring, be sure to see the cherry blossom trees blooming in Tom McCall Waterfront Park.
Every spring, like clockwork, the cherry blossoms in Portland make an appearance that kicks off the official start of sunny and longer days.
The best place to see cherry blossoms in bloom is at Tom McCall Waterfront Park which is located in downtown along the Willamette River.
In the park are one hundred Akebono cherry trees that line the waterfront and in spring, the trees branches explode with pink, delicate flowers that decorate the landscape.
The best time to view spring bloom here is between mid-March and early April.
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 three hundred types of vacuum cleaners displayed here. If you’re looking for weird things to do in Portland, this tops the list!
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
Photo by Travel Portland
Rose City Rollers is one of the largest modern roller derby leagues in the United States, if not the world.
It comprises a multitude of teams at various levels of competition with games hosted at The Hangar at Oaks Amusement Park where they draw up to 22,000 fans a year for games!
You can watch these fast and furious hometown girls (with names like Scald Eagle) battle it out in the rink.
Settle into a bleacher, grab some popcorn and beer, and see how the city of Portland rolls. Check the schedule for games here.
16. Shanghai Tunnels
Portland was once known as the Forbidden City for its illegal practice of shanghaiing.
What is ‘shanghiing’? It is the practice of kidnapping men and selling them as slaves to ship captains in need of crew.
Local lore has it that a labyrinth of interconnected basements and underground tunnels ran to the waterfront making it easy to sneak illegal goods including shanghaied victims, between shore and ship.
The tunnels, which lie under Old Town Chinatown, can be explored, but only with a local tour group.
You can explore the tunnels on this Portland Underground Shanghai Tunnel 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 though.
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
The Oregon Museum of Science and Industry is a science and technology museum in downtown Portland. It contains three auditoriums, a large-screen theatre, planetarium, and exhibition halls with a variety of hands-on permanent exhibits.
Take in a lecture about tornadoes or tarantulas, study the science of beer, or experience a movie in a brand-new way. Every month offers something different!
Photo by Justin Katigbak - Travel Portland
The Portland Art Museum was founded in 1892 making it the oldest art museum on the west coast and seventh oldest in the USA.
The museum’s art collection is housed across two historic buildings in Portland’s cultural district. The collection is distinguished for its holdings of art of the native peoples of North America, English silver, and the graphic arts.
21. Take An Art Walk
Art Walk in Portland, Oregon
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. Go Spirit Tasting At A Distillery
Photo by Travel Portland
Love your hard liqour? Yes? Then take a trip to Distillery Row where twelve independent distilleries produce everything from gin to rum, whiskeys, and other uniquely flavored spirits.
You can find these locally handcrafted drinking establishments in the Southeast and Northwest districts of Portland.
23. Sample Flights At A Portland Brewery
Portland may very well be the Craft Beer Capital of the World with over sixty breweries in town! You simply must stop in at least one local brewery and sample some of the magic created here.
Brewmasters in Portland add copious amounts of hops to create IPAs that include flavors reminiscent of everything from pine to grapefruit.
But don’t worry if IPAs aren’t your thing, the breweries here have all the bases covered including lagers and sours too.
Some of the best breweries to check out in town include Rogue and Deschutes.
If you would prefer some company as you explore the city’s numerous breweries, there are several group-led tours you can join such as this three hour Brew & Bicycle Tour that explores downtown, the Pearl District and Northwest Portland.
There’s even this haunted brewery tour where you can sample local beers as you walk through 19th century buildings and listen to stories about Portland's era of kidnapping, gangs, prostitution and opium dens.
Top-Rated Brewery Tours In Portland:
24. Stumptown Coffee Roasters
Stumptown Coffee Roasters, who got their start in 1999, have been convincing their customers that they are the best coffee roasters in the nation ever since.
Stumptown has grown to become a massive brand with locations in cities that include Seattle, New York, Los Angeles, and even New Orleans.
If you love your coffee, you will definitely need to try Portland’s most famous coffee roaster while you’re in town. They have four locations, two cafes in the downtown area, and two cafes in Southeast Portland.
25. Pine State Biscuits
For the best southern style breakfast and brunch in town, be sure to stop in at Pine State Biscuits.
This restaurant has mastered the art of buttery and flaky homemade biscuits which are topped with tender buttermilk breaded chicken.
Diners can choose from a mouthwatering sausage gravy or the most delicious mushroom gravy.
The most popular biscuit with locals is the Reggie Deluxe which combines fried chicken with bacon, fried egg, and cheese. It is unbelievably good!
26. Voodoo Doughnuts
Voodoo Doughnuts might just be the most well-known donuts in the nation.
Famous for their large donuts slathered in colorful frosting and topped with cereal and candy, these dangerously sweet treats consistently top every Portland bucket list under best things to do.
While some may argue that these donuts don’t taste as amazing as they look, it hasn’t seemed to stop the droves of people who line up every day to get into the flamboyantly painted and decorated shop in downtown Portland.
If you haven’t sampled Voodoo Doughnuts before, you simply must stop in during your trip to Portland and try them at least once in your lifetime.
Feel free to come back to this article after you’ve eaten one of these Instagram-worthy desserts to let us know what you thought!
27. Doe Donuts
Doe Donuts is another popular donut shop in Portland but these donuts are notable for being vegan and made from scratch using quality ingredients.
Doe offers year-round and unusual seasonal flavors so you’re bound to find something that tickles your fancy.
28. Departure
Departure sits on top of five-star The Nines Hotel in downtown Portland. This top-rated restaurant offers innovative modern Asian cuisine.
From street food-styled starters to noodle specialties and sushi, Departure embraces the bounty of the Pacific Northwest to deliver the fiery flavors of the Far East. They also boast the largest sake list in Portland.
One of the reasons this restaurant makes this Portland bucket list is because of the spectacular skyline views that can be seen from this roof-top restaurant.
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 popular ice cream shop in Portland a visit.
30. Tea Tasting at Smith Teamaker
If you enjoy sipping tea, you simply must stop in at Smith Teamaker. Make sure you order a tea tasting which is basically just like ordering a flight of beer but obviously with tea instead.
You can choose four varieties from the menu including black and herbal teas. They also serve lattes and iced concoctions alongside handmade pastries.
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.
Some of the best places to find food trucks include the 5th Avenue Food Cart Pod, Hinterland Bar & Food Court, and one of the longest established of all, 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 here are cooked in bacon fat then tossed with fried herbs and Parmesan. Mmmm delicious!
Pok Pok is on every foodie’s Portland bucket list for their famous chicken wings. Seriously, people come from all over just to eat at this Portland restaurant. We recommend checking out their other store, Pok Pok Wing too.
34. Wasabi Sushi PDX
Who doesn’t like sushi? One of the best places to for sushi in Portland is Wasabi Sushi PDX who make Instagram-worthy sushi donuts, sushi burgers, and sushi b-rittos (sushi rolls wrapped in spicy cheetos)!
You can also order poke bowls and delicious ramen noodles here too.
35. The People’s Pig
Killer barbecue and delicious cocktails make The People’s Pig one of our favorite places in Portland to grab lunch.
SHOPPING IN PORTLAND
36. Portland Saturday Market
Photo by Justin Katigbak - Travel Portland
The Portland Saturday Market is a beloved open-air market that has been in operation since 1974! At these markets you’ll find over one hundred local vendors selling handmade arts and crafts like jewelry, paintings, pottery, photographs, and clothing.
Besides arts and crafts, the Saturday Market also hosts a number of food trucks offering everything from Indian to Mexican, Mediterranean, and more.
If you’re looking for Pacific Northwest inspired artistic pieces, be sure not to miss visiting this classic Portland attraction.
The markets are located adjacent to the Willamette River in downtown Portland.
37. House of Vintage
House Of Vintage in Southeast Portland
Portlanders are people who prefer unique, one-of-a-kind clothing pieces as opposed to trendy fast fashion.
The locals here love shopping for vintage clothing, and the city has a plethora of small businesses selling second-hand items making it one of the best locations in the U.S. for thrift store shopping!
Portland’s southeast district, particularly Hawthorne Street, is the best place to go vintage store shopping.
If you’re interested in hunting for unique treasures, be sure to stop in at House Of Vintage, the city’s best place to hunt for vintage clothing.
This massive store houses many different dealers with their own inventory selling everything from clothes to shoes, accessories, furniture, and collectibles.
38. Buffalo Exchange
One of the most popular places to go thrift store shopping in Portland is at Buffalo Exchange. They actually have two store locations; one in downtown Portland on Burnside Street, and another in the Hawthorne District.
At Buffalo Exchange you’ll find a wide variety of vintage pieces, secondhand clothes and shoes from big brand names at hugely discounted prices, accessories, jewelry, and even sporting equipment.
They even except exchanges so if you’re looking to get rid of some old items, you can swap them out for store credit or accept cash payment.
39. Powell’s Books
Powell’s City Of Books on Burnside Street in downtown Portland.
One of Portland’s most famous landmarks is the Powell’s City of Books. This place is literally a multi-level maze that you could easily get lost inside.
It is the largest new and used bookstore in the world, therefore it deserves to be on every Portland bucket list.
Covering an entire city block, the store encompasses 68,000 square feet and contains over one million books!
Grab a coffee from the attached coffee shop and spend some time roaming through the book shelves.
NIGHTLIFE IN PORTLAND
40. Watch A Movie At A Brew Cinema
Photo by Justin Katigbak - Travel Portland
It’s no secret Portlanders are fond of beer so naturally cinemas throughout the city offer adult beverages during screenings.
If you’re looking for a low-key activity during your trip to Portland, consider a night out at a Brew Pub.
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 forty years now.
For a unique way to spend your night out in Portland, join the interactive crowd for a screening of one of the longest running films in history.
Doors open 11:30pm every Saturday night and the show starts at midnight.
42. Doug Fir Lounge
The Doug Fir Lounge is a cozy restaurant and live music venue that regularly hosts national and international touring performers.
Since its opening in 2004, this establishment has become one of the finest music venues in the city known for its indie music scene.
The venue itself is very cool and was designed by an internationally renowned architect. Its interior is reminiscent of an urban ski lodge filled with textured woodwork and glass, with outside walls clad in logs.
If you enjoy live music, be sure to check out Doug Fir’s upcoming shows here.
You can find the Doug Fir Lounge on East Burnside Road inside the Jupiter NEXT Hotel. The restaurant and bar is open seven days a week from 7am to 1am.
43. Crystal Ballroom
The Crystal Ballroom enjoys national recognition for a reason. No local venue, and indeed few in the nation, can challenge this elegant ballroom’s more than one hundred years as a premier place to hear live music, dance and have memorable experiences.
Today, the Crystal Ballroom, which is owned by McMenamins, is still thriving and the best place to see live music whether it’s country, indie, hip hop, or metal.
If you’re looking for a night out inside a historical venue, be sure to check the Ballroom’s events calendar to see if anyone you like is performing.
44. Hawthorne Theater
Over the course of its nearly one hundred year history, the Hawthorne Masonic Building, which currently holds the Hawthorne Theatre, has donned many different hats, each no less interesting than the last.
From its humble beginnings in the early 1920s as the Eastside’s central meeting place for Masons, to its more recent foray into live music venue, the Hawthorne Masonic Building has become a Portland institution in and of itself.
The present day Hawthorne Theatre is one of the few places left in an ever-changing Portland to see all-ages shows, and hosts everything from metal shows to dance nights, comedians to art shows, and everything in between.
The contrast between contemporary musical acts playing in a building steeped in history is part of what makes this venue so unique.
If you’re looking for a fun night out, consider seeing an up and coming act inside one of Portland’s most historic establishments. See the calendar of events here.
45. Helium Comedy Club
Helium Comedy Club is an entertainment venue that hosts world class talent inside an intimate theater on a weekly basis.
Guests can enjoy live comedy during two hour shows that include an opening act and a feature artist in addition to the headlining act.
There is no need to dine out before arriving because the venue serves appetizers, entrees, desserts, as well as craft beer and cocktails.
See their calendar of events here.
46. Dante’s
Dante’s is an iconic rock den in downtown Portland that hosts nightly entertainment from bands to cabaret, burlesque shows, and karaoke.
This establishment has a dive bar like feel although the venue itself is quite large. Inside, the walls are painted in a devilish black and red, with tables placed in front of the stage. A cozy firepit is situated at the back of the venue for those cold winter nights.
Dante’s has a colorful history of debauchery reputed to have changed hands between bordellos and liquor distributors before becoming a punk bar to what it is now. They always have something happening so pop in and see if its something you like.
47. Moda Center
Whether you’re into music or sports you should check out the events calendar for the Moda Center to see if your favorite entertainer or sports team will be performing or playing on your travel dates.
The Moda Center is the home of the Portland Trailblazers so you may be able to catch a game during basketball season.
Big artists like The Who, Florence & The Machine, and Post Malone, are always headlining at this venue and catching your favorite musical act would certainly make your trip to Portland a more memorable one.
DAY TRIPS FROM PORTLAND
49. Chase Waterfalls In The Columbia River Gorge
Multnomah Falls
Take a day trip out to the Columbia River Gorge and see Oregon’s tallest waterfall Multnomah Falls. This magnificent cascade is 620 feet high and is beautiful to see no matter what time of year it is.
There are many other stunning waterfalls in the Columbia River Gorge that you shouldn’t miss seeing while you’re in the area.
The Columbia River Gorge is only a short thirty minute drive from Portland. You could rent a car and drive yourself out there, or join this popular Portland City Sightseeing Tour which includes a trip to the Columbia River Gorge, or head straight out there on this cheaper Columbia Gorge Tour.
50. Visit A Winery
The Willamette Valley, which is home to over two hundred and fifty wineries, 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 Willamette Valley.
WHERE TO STAY IN PORTLAND
The Nines - If you’re looking for a five star experience, choose to stay at The Nines, a luxury hotel in downtown Portland. This hotel features two restaurants, a bar, and rooftop terrace.
Rooms here are a visual indulgence and feature satin drapes, electric fireplace, and original artwork by the students at Pacific Northwest College of Art.
Rest on robin blue pillows and under delicate Frette linens.
Kimpton Riverplace Hotel - This refined hotel sits on the Portland river front offering water views from most guest suites and cottages.
Guests of the Kimpton will enjoy complimentary tea and coffee each morning and a nightly hosted wine hour every evening in the lobby.
The Porter By Hilton - For an affordable yet still luxurious, look into staying at The Porter, a modern and stylish hotel located in downtown Portland.
Rooms here feature luxurious robes and slippers, premium bath amenities, in-room premium Italian coffee service by Caffé D'arte, and a deluxe Waldorf Astoria bed.
Search for more hotels in Portland below.
Read Next
7 Reasons You Should Visit Portland, Oregon
Stunning Waterfalls Easy To Reach From Portland
Guide To Visiting Multnomah Falls
Best Things To Do In The Columbia River Gorge
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