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.

Portland Bucket List: Fun Things to See, Do & Eat

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WHAT TO SEE + DO

1. ✦ 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!

2. ✦ 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.

3. ✦ 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 this day it was a single, teeny tree surrounded by a trio of miniature green bushes.

4. ✧ Partake in a River Float

5. ✦ 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!

6. ✧ See the Oldest Drag Queen at Darcelle XV Showplace

7. ✦ Hike to The Witches Castle at Forest Park

Didn’t I tell you that Portland had some strange, yet interesting things going on? 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. It still a fun spot to tour and learn about the tragic history that surrounds the place.

8. ✦ 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.

9. ✧ 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.

10. ✧ Soak in the Pool at Kennedy School

11. ✦ Smell the Roses at a Rose Test Garden

Portland’s International Rose Test Garden’s 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.

RELATED: A Love Story Through an International Rose Garden

   

12. ✦ 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.

13. ✧ Walk in the Towering Redwood Grove Hoyt Arboretum

14. ✦ Get Lost in Powell’s Books

I was reluctant to include this goal here because it seems to be on every “Things to Do in Portland” list and it is “just a book store”. But, then I went to Powell’s Books flagship location that is home to more than one million books. It is way more than just a book store.

The cookbook section, complete with a vintage selection, would be enough to keep me coming back to Powell’s. Consider adding it to your Couple’s Bucket List, as it would be a great way for you and your spouse to pass a Portland rainy day.

15. ✧ 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.

16. ✦ 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.

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17. ✦ Pose with the Paul Bunyan Statue

18. ✧ Feel the Peace at the Grotto

19. ✧ Attend the Naked Bike Ride

For all intents and purposes, the Naked Bike Ride has a good course behind it; it shows and garners support for human powered transportation thus minimizing our carbon footprint. That being said, this clothing-optional event is a spectacle the likes of which you probably haven’t seen…ever.

Have you ever seen a streaker run past you? Now imagine hundreds…thousands of naked people leisurely riding on bikes as if there was absolutely nothing wrong with that! If there was ever any activity you wanted on your bucket list to remind you of when you were young and reckless, this would be it.

20. ✦ 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.

21. ✧ See the Works at Portland Art Museum

22. ✦ 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.

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23. ✧ Ride the Aerial Tram

24. ✧ 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!

25. ✦ Take a Road Trip to Multnomah Falls

Technically, this is not in the Portland city limits, but it is a bucket list worthy thing to do that is on the Oregon side of the Columbia River Gorge, only a forty minute drive East.

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.

Book a Tour: Multnomah Falls and Columbia River Gorge Half-Day Tour
Book a Tour: Full Day Wine & Waterfall Tour

 

26. ✧ See the Belmont Goats

27. ✧ 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. You can explore this with the Portland Underground Walking Tour.

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WHAT + WHERE TO EAT

28. ✦ Eat a Bug Sundae at the 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 you can 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!

30. ✧ Shop at the Saturday Market

31. ✦ 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.

Related: Do a Liquor Tasting at a Portland Distillery

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32. ✦ Eat 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.

33. ✦ Eat the Biscuits at Pine State Biscuits

34. ✦ Try the World Famous Wings at Pok Pok

How can chicken wings be this addictive and cult-forming is beyond me. But, they can. The Vietnamese chicken wings at Pok Pok are layered with flavor and the absolute best wings I have ever eaten in my life . Plus, just like the traditional fried wings from Buffalo, you can order them mild, medium or spicy.

Try this recipe to make your own at home: Ike’s Fish Sauce Wings

35. ✦ Get Tacos at ¿Por Qué No?

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

37. ✦ Eat Pigeon at Le Pigeon

There are not too many restaurants around the world that offer pigeon on their menu. So, when you find one that does you must take the bucket list opportunity to eat one. Le Pigeon in Portland is that restaurant.

Their menu changes so confirm ahead of time what form of pigeon they are featuring on the menu. On the evening I had a delightful dinner there they were making pigeon with liver toast, grapes and white anchovies.

Bucket List bonus: Le Pigeon also sporadically features a variety of offal on the menu. So, this is your opportunity to eat things like sweetbreads, heart and cheeks.

Related: Have an Adventurous Meal of Pigeon, Heart & Cheeks

38. ✧ Pick Berries at Kruger’s Farm

If you are looking for a nice, quiet and homey farm to just relax and get fresh produce, then you might want to head out to Kruger’s Farm. A little outside of Portland city center on your way to Highway 101, you will find a 150-acre slice of organic paradise. At Kruger’s Farm you can pick a wide variety of berries, sample local farm produce and indulge in some sweet honey.

39. ✧ Get a Taste of India at Bollywood Theater

40. ✦ Do a Tea Tasting at Smith Teamaker

Doing a tea tasting at Smith Teamaker is similar doing one at a local distillery, you select four 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.

Related Article: Wear a Fez at a Portland Tea Tasting.

41. ✦ Get Ice Cream at Salt & Straw

42. ✦ Drink a Cup of Stumptown Coffee

This 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. Go one step further than simply drinking a cup of Stumptown by visiting The Annex location to get a coffee education and do a free tasting.

43. ✦ Drink Oregon Wine

44. ✧ 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.

45. ✦ And yes—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.

Related Article: Eat the Old Dirty Bastard at Voodoo Doughnut

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.

TIP: Many of these places can be reached with the Big Pink Hop-On Hop-Off Trolly that has 14 stops.

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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:

• Full-Day Wine & Waterfalls Tour
• Underground Portland 2-Hour Walking Tour
• Best of Portland 2-Hour Walking Tour

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Related

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

More Resources

Portland Tours with Get Your Guide
Streetwise Porland Map