From strolling through Chinese and Japanese gardens to taking part in a naked bike ride without getting arrested for public indecency, there are really cool as well as weird things to do in Portland, Oregon. The city has been voted one of the most popular in the U.S and as soon as you visit, it is easy to see why. The people are friendly; they are environmentally conscious (most residents ride their bikes through the city as opposed to taking a cab), plus there are plenty of fun activities.

And then there are your typical city attractions such as excellent dining, a great bar scene and thrilling historical monuments that will keep you busy throughout your stay. If you haven’t been yet, here are some of the best reasons why you should add Portland, Oregon to your bucket list.


The Best Attractions, Activities and Fun Things to Do in Portland, Oregon


WHAT TO SEE + DO

1. Attend the Naked Bike Ride

Have you ever seen a streaker run past you? Now imagine hundred, if not thousands, of naked people leisurely riding on bikes through the city! The Naked Bike Ride is a clothing-optional event that is an unique once-in-a-lifetime attraction not to be missed, even if you are not participating. Showing support for the event is showing support for human powered transportation and minimizing our carbon footprint..


2. Do an Escape Room

Portland Escape Room is known to offer live games where participants are locked in themed rooms for an hour and left to solve puzzles in order to find their way out. They offer an immersive, fun, and entertaining way of engaging your brain as you compete with other participants.


3. Enjoy at Portland’s Shakespeare in the Park

Portland Actors Ensemble is one of the oldest theater groups in this city, and on of their best shows is Shakespeare in the Park. They are renowned to feature actors who have the power to transform lives with their plays. The entire content usually features heartbreaking, hilarious, and thrilling plays with powerful illusions. 


4. Enjoy The Thrill Of Racing At Portland International Raceway

For a little adrenaline rush, head over to Portland’s International Raceway to watch the cars whiz around the track. They host different racing cars including the NASCAR and IndyCar races, in addition to many others. 

Enjoy The Thrill Of Racing At Portland International Raceway


5. Explore Pittock Mansion

Pittock Mansion is a sandstone beauty that was home to two of Oregon’s most iconic pioneers (Henry and Georgiana Pittock) and it is breathtaking in its own right. Built in 1914, this 22 room mansion features a combination of Victorian design and a heavy touch of French-Renaissance.

The guided tours of the mansion will give you clear insight on how the high life was enjoyed in Portland a few decades back. There are 46 acres of lush ground around the property and mind-bogglingly beautiful views of Portland, Mount St. Helens as well as Mount Hood. It is definitely worth a visit, if for nothing else but the beautiful selfies opportunities you will find.

FYI: The Portland City Tour will make a stop there, PLUS Pearl District, Pittock Mansion, Alberta Arts District!


6. Explore Portland by Bicycle

With the availability of bike rentals and diverse bike routes, there is no better way to explore the districts and small locales in this city than doing it on two wheels. This will give you a great opportunity to cycle as you take in the expansive views with different backgrounds.

Explore Portland by bicycle


7. Explore the Districts

There are almost 100 districts in Portland, and each offers their own fun things to do, but it will be hard to visit all the attractions and activities, so just do a few. The top districts of Alberta, Pearl, and Mississippi are known for their street fairs, rivers, art scene, and tasty restaurants. 


8. Explore the Shanghai Tunnels

During the period between 1850 and 1941 Portland was known as the “Forbidden City of the West.” This is because it was one of the most dangerous ports in the U.S, if not the world. Within this period, a series of tunnels, known as the Shanghai Tunnels was developed under the city streets.

These tunnels linked a wide web of hotels and basement bars to each other and to the docks at the Willamette River. They were also used to ferry goods, people, supplies as well as a host of other illicit activities to and from the ships that visited the docks at Portland. For a time, able bodied men were drugged and smuggled through these tunnels to work on forced labor basis as crew men on ships that needed the workforce. This elaborate web of tunnels is surrounded by fantastic legends of horrific tales that will send a chill down your spine. 


9. Feel the Peace at the Grotto

With the chaos of life that surrounds us every day, sometimes it’s just right to take a downtime and rest. If you are looking for a peaceful thing to do in Portland, then The Grotto is a great avenue where you can experience serenity. The national sanctuary has a peace garden, meditation chapel, rose garden, and even shrines. This is where you can get your soul nourished and rejuvenated in a natural way.


10. Get A Glimpse Of Life On A Submarine

Have you ever imagined how life is while you are in a submarine? Well, this Oregon city gives you the best opportunity to view life from a different angle at the Oregon Museum of  Science and Industry. The tours will have you a peek into crew life, plus you will get to look through the periscope and even touch a torpedo!

Get A Glimpse Of Life On A Submarine


11. Get Lost in Powell’s Books

Powell Books is on just about every Things to Do in Portland list, and you may wonder what could be so special about a book store. Well Powell’s is way more than your average shop, their flagship location is home to more than one million books! The cookbook section, complete with a vintage selection, would be enough to keep me coming back to Powell’s. 


12. Go to a Brewpub Movie Theater 

What’s better than a night at the movies with buttery popcorn? A night at the movies with buttery popcorn and BEER. McMenamins Bagdad Theater is a relic of Hollywood’s golden age and a place to enjoy a slice of pizza while drinking a cold, hand-crafted ale. Don’t worry if you are a wine lover like me, they have that too.


13. Go to the Oregon Historical Museum

With three floors of exhibits, the Oregon historical Museum is filled with over 85,000 artifacts and documents related to Oregon and America. While there, don’t miss seeing the famous Portland Penny that was used to decide the name of the city.


14. See a Portland Center Stage Show

Portland Center Stage is the biggest theater company in this city and it’s known to produce professional theatrical content for the surrounding community. Though the company was established in 1988, its home is at The Armory which was originally built in 1891. Besides the incredible entertainment, the buildings Romanesque revival architecture style is also sight to behold. 


15. Have Fun in ‘Portland’s Living Room’

The Pioneer Courthouse Square is a 40,000-square-foot city block in the middle of the city where people gather for one of their 300 planned events or just hang out and socialize. Described as Portland’s living room, this urban gathering space is one of the most visited places in Porland.

Signages at Pioneer Courthouse Square


16. Hike the Columbia River Gorge

Hiking gets interesting, challenging, and of course, fun as you navigate the Columbia River Gorge. Just 30 miles east of Portland you’ll find this is a beautiful area filled with waterfalls, vistas and epic hikes. 

Hike the Columbia River Gorge


17. Hike to The Witches Castle at Forest Park

Portland has some weird, yet interesting things going on, and this is one of them. An easy half-mile hike from the Upper Macleay Parking lot near the Portland Audubon Society, or a slightly longer three-quarter mile jaunt starting from the Lower Macleay Parking lot at NW 30th and Upshur will lead you up to the Witches Castle at Forest Park.

Despite its name, the Witches Castle has nothing to do with witches. Although the ruins have a long history of tragedy dating back to the 1800’s, it was dubbed the Witches Castle by High Scholars who started holding kegger parties there in the 1980’s. 


18. Make a Quick Stop at Starks Vacuum Museum

In downtown Portland, there is a store called Stark’s Vacuum Cleaner Sales & Service that does a lot more than just sell you vacuum cleaner. Tucked away in a corner of the store is an interesting collection of ancient vacuum cleaners that will highlight the sharp contrast between modern day technology and that of yesteryears.

If you are a history buff (or just looking for some quick amusement), then you will absolutely love the more than 300 different types of vacuum cleaners lined up on the walls. There is even one that required two people to operate!

Annette at The Starks Vacuum Museum


19. Partake in a River Float

Spring and summer periods are incomplete in Portland if you don’t grab your inner tube and partake in a river float. This is almost like a ritual for the residents as well as visitors who love the livery that the river tubing activities and kayaking expeditions that the river floats offer. 

Some of the best places to do your float include Sandy River, Clackamas River, East Fork Lewis River, and Deschutes River.


20. Pay tribute at Oregon Holocaust Memorial

You can pay homage to those who lost their precious lives during the Holocaust period by visiting the Oregon Holocaust Memorial. This Oregon Jewish Museum is also the best place for you to share your loved one’s memory .


21. Play a Round of Glow in the Dark Mini Golf

The Glowing Greens is a black light miniature golf adventure good for the entire family. The glow in the dark neon is sure to add a new twist to a regular game of mini golf. Plus, it’s a bucket list bonus if you get a hole in one!


22. Portland Free Walking Tour

A walking tour provides a fun way to explore Portland and get to know all its little secrets. The Secrets of Portlandia offers a free walking tour will not only take you to the tiny unknown corners and least traveled streets, plus give you insider tips for attractions, restaurants and activities not to miss.


23. Pose Under the Keep Portland Weird Sign

The Keep Portland Weird slogan is meant to embrace the uniqueness of the city and support local businesses. You will see the saying on bumper stickers throughout the town, but no sticker is quite as impressive as the huge painted wall located just South of the Burnside bridge.

Bucket List bonus: Voodoo Doughnuts is right across the street!


24. Gawk at the Paul Bunyan Statue

The huge Paul Bunyan Statue, of the famous mythical logger, sits in Portland’s Kenton neighborhood (see map). The gigantic novelty is made of metal and concrete, and is an attention grabber that deserves to feature in your camera roll.


25. Ride the Aerial Tram

The Aerial Tram is a unique transport system that offers amazing high views of the city and the area beyond. The tram usually operates on load and go, with cabins departing approximately every 5 minutes. 

A view in an Aerial Tram in Portland


26. See a Performance at Revolution Hall

Revolution Hall is a world-class venue and the ultimate rock n’ roll high school,  since is located within the former Washington High School. The 830-seater hall normally features top-notch performers with different genres of music and entertainment.


27. See the Belmont Goats

This is definitely one of the top things to do in Portland Oregon. The Belmont Goats provide the public with a quirky and carefree way to bond with animals. They are normally interested in human attention, from fur brushing to scratching.

Belmont Goats in Portland


28. See The Cherry Blossom Bloom At Tom McCall Waterfront Park

To perfectly see the cherry blooms, then head over to the Steel Bridge. There are 100 Akebono-cherries that line the Tom McCall Waterfront Park and when they blossom, the whole area comes to life. This spot is usually packed during the spring season, so make sure that you arrive early to beat the traffic.

See The Cherry Blossom Bloom At Tom McCall Waterfront Park


29. See the Jetliner in the Woods

There are private planes that are so luxurious they even make for better homes than your typical million dollar mansions…and then there is the Jetliner in the Woods. Way out there in the woods of Oregon’s wine country, is a 727 jetliner that has been transformed into a home by the owner, Bruce Campbell. An attraction in itself, this massive air craft makes for good story telling as you begin to wonder how he got it up there and why he would want to.

See the Jetliner in the Woods


30. See the Oldest Working Drag Queen at Darcelle XV Showplace

Darcelle XV is the oldest female impersonator on the West Coast. He’s an absolute legend when it comes to Portland’s entertainment space. Together with his company, they are known to entertain the audience with comical skits and plays that are full of Las Vegas-style glitz and glamor.


31. See the Smallest Park in the World

At the intersection of two streets in Southwest Portland, located in the center divide, you will find Mill Ends Park. At a whopping 452 square inches it is recognized by the Guinness Book of World Records as being the smallest park in the world.

The spot was actually meant for a light pole, but when that failed to happen it was turned into this minuscule piece of prime real estate. The landscape sporadically changes, but on the day I went it was a single, teeny tree surrounded by a trio of miniature green bushes.


32. See the Works at Portland Art Museum

Portland Art Museum is one of the best places where you will experience the power of art in the city. The internationally renowned museum offers an exciting experience with major exhibitions that is rich in Northwest and Native American collections.

See the Works at Portland Art Museum RF 3


33. Seek out Street Art Around the City

One thing that’s a guarantee when you are out in Portland Oregon is that you will come across a wide range of art collections. This city’s streets consist of a booming art scene and with the availability of walking and biking lanes, you can explore all the hidden spaces. Use this map to find some of the best!


34. Sit Ringside at a Roller Derby Bout

A roller derby bout at Rose City Rollers is filled with hard hits, fast feet and sometimes accented with alterations between the female players. This rowdy indoor sport will get your heart pumping while you root for your favorite team member.


35. Smell the Roses at a Rose Test Garden

Portland’s International Rose Test Garden is the oldest public garden of its kind with a primary purpose of testing rose varieties. Before visiting I thought I wasn’t a rose girl, but these aren’t your typical supermarket flowers. They come in all shapes, colors, sizes and have unique names like Hot Tamale, Walking on Sunshine and Grand Amore. 

PS: you could sign up for the half-day city tour that takes you to the garden plus Pittock Mansion! 


36. Soak in the Pool at Kennedy School

Not only is the soaking pool at McMenamins Kennedy School ideal for optimal relaxation, it is also a ceramic work of art! The pretty pool is located where the teachers lounge used to be and is surround by gardens.


37. Stroll Though the Japanese Garden

Portland’s 5.5 acre Japanese Garden is influenced by Shinto, Buddhist, and Taoist philosophies. It is comprised of five garden styles, each one more beautiful than the last. Strolling through this environment will transport you to the gardens in Japan.

Make a day of it: The Japanese Garden is next to the International Rose Test Garden, so visiting both in one day is possible.


38. Stroll through Lan Su Chinese Garden

Dubbed by many as ‘the most authentic Chinese garden outside of China, the Lan Su Garden is serenity personified. This walled garden will instantly transport you out of the U.S to China as soon as you walk through the gates.

Lan Su Garden can be loosely translated to mean the “Garden of the Awakening Orchids.” That is exactly what you will experience as you explore Chinese culture, see their way of thinking and learn a bit about their history.

For something super unique, take the Downtown Ghost Tour that starts at Lan Su Garden.


39.Take a Road Trip to Multnomah Falls

Technically, this is not in the Portland city limits, but it is so bucket list worthy that you will want to take the 40 minute drive East to the Columbia River Gorge to see it. It is one of the best things to do in Portland! Multnomah Falls is split into two sections for a total of 611 feet and every inch is stunning. It is quite a sight from the ground floor, but you can also take a hike to walk across the bridge and on to the top.

These highly rated tours will take you there:


40. Take Pictures in the Photo Booth at Ace Hotel

At first, this might not sound like anything spectacular. After all, we have all been to a photo booth or two in our lives before, so what’s so special about this one? Well, the photo booth at the Ace Hotel in Portland is ancient. We are talking photographic technology from a hundred or so years ago. It uses the same process that was used way back when silver film was the rage.

You have to wait just a few minutes for the images to develop and it is quite an experience, so leave your iPhone in your room and take selfies in the photo booth at Ace Hotel.17.


41. Visit Crystal Springs Rhododendron Garden

This is an internationally recognized garden with a scenic spring-fed lake that surrounds it. The Crystal Springs Rhododendron is ideal for recreation as well as events. Have fun here during the day exploring different plant species including the vibrant rhododendrons in their full bloom.


 

 

42. Visit Some Willamette Valley Wineries

Renowned to be home to over 700 wineries and one of the leading wine producers in Oregon, Willamette Valley is the best place to take a wine tour. It’s about a 40 minute drive from Portland, but it is a must-do if you are a wine lover like me! There are plenty of wineries to choose from (you can find your favorites on the Williamette Wines website, but if you have a hard time picking just the right one, then check out Wine Country’s top eight Wiliamette wineries not to miss.

The 5-Hour Willamette Valley Wine Tour with Tastings will give you a great sampling of local wines or opt for the Wine and Waterfalls Day Tour.

Visit Willamette Valley Wineries


43. Walk Through the Towering Redwood Grove Hoyt Arboretum 

The Redwood Grove at Hoyt Arboretum is a living museum with almost 70 trees, some planted as far back as 1931. Designed to conserve the endangered species in Oregon and educate the community, Hoyt Arboretum is also a 190-acre arboretum that’s perfect for outdoor activities including hiking trails.


WHAT + WHERE TO EAT

44. Do a Spirit Tasting at a Distillery

Amongst industrial warehouses and businesses in Portland lies a handful of distilleries which produce an array of unique liquors. This frequently visited area is known as Distillery Row and once you need a break from the downtown pubs, you must venture to do a spirit tasting at a Portland Distillery.

Spirit Tasting at a Distillery


45.  Do a Tea Tasting at Smith Teamaker

Doing a tea tasting at Smith Teamaker is similar doing one at a local distillery, you select a few varieties from the menu to compare and contrast. The flight can be all black teas, like the Lord Bergamot or all herbal infusions, like the Big Hibiscus. If you are unsure of what to choose, ask the knowledgeable staff to guide you with your selections.


46. Drink a Cup of Stumptown Coffee

Stumptown Coffee is all the rage in Portland and I did due diligence by hunting for others, but Stumptown always came out on top. They source the best coffees from all over the world and you can taste it in every cup. 

Drink a Cup of Stumptown Coffee


47. Drink a Flaming Spanish Coffee

A Flaming Spanish Coffee at Huber’s consists of Bacardi 151 rum, Kahlua, Bols Triple Sec, coffee, fresh whipped cream and a touch of nutmeg on top. But, what makes this drink a special thing to do in Portland is the execution that involves a fire-filled show, prepared table-side and with lots flair.

Drink a Flaming Spanish Coffee


48. Drink Liquor in Detention

McMenamins Kennedy School is an old elementary school turned into an entertainment haven. You can sleep in one of their guest rooms, eat in the Boiler Room and watch a movie in the comfy theater. Plus, if you have ever been late to class or offended a teacher you are able to pay your penance in the Detention Bar where they will serve you beer, wine, single malts or bourbons. That sounds like my kind of detention.

An old room where you can drink


 

49. See the Oddities at Freakybuttrue Peculiarium

Who wouldn’t want to visit a place with a name like the Freakybuttrue Peculiarium?  It is filled with creepy oddities and experiences, like the opportunity to have your photo taken getting an alien autopsy or viewing a dollhouse where one of the rooms had a bloody massacre. Not only is it bizarre (and free), but when I was there you could also order a Bug Eaters Delight sundae before leaving. It is topped with real bug larva and if you dare to eat it your photo will make it onto the Insectarian Club Hall of Fame. Look for my picture there!


50. Eat a Voodoo Doughnut

I will admit that the base of Voodoo Doughnut’s taste just like the rest to me, but what makes this the hot spot in Portland is the unique flavors that that have. The Marshall Mathers is covered in M&Ms to signify the rapper Eminem, the Loop Donut is covered in Fruit Loops and the Dirty Snowballs have marshmallow topping dipped in coconut and topped with peanut butter.

Everyone talks about the Maple Bacon donut, but my favorite is the Old Dirty Bastard that is covered in crumbled Oreo cookies and peanut butter. If you head over to the Original Location on 3rd Ave., the ‘Keep the Portland Weird’ sign is right across the street.

If you are the ultimate donut lover, then hop on the Underground Donut Tour that will have you sampling four of the best shops in town.

Eat a Voodoo Doughnut - Portland Bucket List


51. Snack on Dirty Fries

What makes dirty fries at Lardo dirty? Pork scraps, marinated peppers, fried herbs and parmesan. These fries can be the perfect side for their popular Pork Meatball Banh Mi or are large enough for a meal on its own.


52. Eat the Biscuits at Pine State Biscuits

If you love a buttery, flaky, homemade biscuit, then get your butt to Pine State Biscuits asap! Whether you order a perfect biscuit sandwich or a more classic biscuits & gravy, your in store for a treat.

A good plate of Pine State Biscuits


53. Food Truck Hop

The food truck scene in Portland continues to boom. You can visit a cluster of them that take up a square block in the city or a solo one in the middle of a retail street or, my favorite, a small corner that contains 5-10 with picnic tables in the middle. There are so many options it will be hard to choose, but for a tasty towering sandwich, hit up Pastrami Zombie for one of their savory ones served on sour rye with coleslaw, Swiss, and your house Russian. Or head or over to indulge in the Poutine fries at Potato Champion.

There’s so many to choose from it’s probably just easier to book a tour, like the Portland Food Cart Walking Tour


54. Get a Taste of India at Bollywood Theater

If you are a fan of sumptuous and mouth watering curries and other spicy, flavorful dishes, then the Bollywood Theater is the best place for you to have a taste of India. Its premium street food is unmatched thanks to the blend of different organic spices. 


55. Get Unique Ice Cream at Salt & Straw

Salt & Straw has what you need to cool that summer heat while you are outdoors, but it’s so good that you’ll want it every season. The chef-driven parlor features delicious small batches of ice creams, handmade using various local ingredients. With flavors like pear & blue cheese and salty donut guava + cheese you’ll want to try them all!


56. Immerse Yourself in the Craft Beer Culture (AKA: Drink Beer)

Just like food trucks, the craft beer scene in Portland is booming! There’s almost 70 breweries which could make it difficult to choose which ones to do your drinking at, but TravelPortland.com can help.  Even easier, the Portland’s Eastside Craft Brewery Walking Tour will take you to multiple breweries!

A beer toast


 

57. Shop at the Saturday Market

Portland’s Saturday Market is recognized as one of the biggest open-air markets in the country, and provides small local businesses with an ideal way of showcasing their crafts and edibles, especially from the Pacific Northwest region.

. . .

From fun activities to quirky attractions to breathtaking nature, there is no shortage of cool things to do in Portland, Oregon. In fact, I advise you to make a list of your favorite must-do things before you visit. Otherwise you may get sidetracked and miss out on a few of the most exciting bucket list activities in Oregon.


Essential Tips for Visiting Portland

Getting There: PDX is a major hub and most airlines will fly into it. You can easily check for the best fare deals at Skyscanner. You can also use choose ‘cheapest month’ as the departure to find the lowest priced dates to fly to your destination.

Where to Stay in Portland: It’s almost always best to stay in a popular district or at least near public transportation. The Porter Portland (luxury) and The Duniway Portland (moderate) are good choices in downtown Portland. For a truly unique bucket list experience stay at Tiny Digs (budget), a budget-friendly hotel of tiny houses. Or search some great deals on hotels of your choice at Booking.com. If you’re looking for more of a home atmosphere (or are traveling with a group of people), head over to Airbnb that has houses, apartments and even just a room for rent in every price range.

Getting Around: If you want to do a lot of exploring then renting a car would be best (that’s what I usually do) and RentalCars.com has some great deals. If you are not renting a car, there are plenty of options. Both Lyft and Uber are available all over the city, plus most of the major attractions can be accessed with the Hop-On Hop-Off Bus. They also have a great light rail and bus system, learn more about them here.

Top Tours: You can find some of the top tours at Get Your Guide. Here are some that I recommend:

This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. You can read my full disclosure here.

You Might Also Enjoy

Visit the 611 Foot Multnomah Waterfall in Oregon
Tell a Love Story Through an International Rose Garden
Do a Liquor Tasting at a Portland Distillery
Eat the Old Dirty Bastard at Portland’s Voodoo Doughnuts
Eat a Bug Sundae at Portland’s Freakybuttrue Peculiarium

Resources

Portland Tours with Get Your Guide
Streetwise Porland Map