Portland is the largest city in Oregon and filled with quirky things to do that range from adventurous to romantic to just plain weird. It is a mix of scenic landscapes, bustling neighborhoods, microbreweries, distilleries and bucket list worthy adventures for everyone.

20 Bucket List Things to Do in Portland

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

1. 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.

SW Taylor St & SW Naito Pkwy, Portland, Oregon | Map | WEBSITE

2. 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.

2234 NW Thurman St, Portland, OR 97210 | Map | WEBSITE

3. 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 (see #16).

SW 3rd Ave (between Burnside and Ankeny) Portland, OR | Map | WEBSITE

4. 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. {photo}

3702 SE Hawthorne Blvd, Portland, OR | Map | WEBSITE

5. Smell the Roses at the International 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. 400 SW Kingston Ave, Portland, OR | Map | WEBSITE

6. Eat at a Food Truck

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. For something unique, hit up PBJ for one of their savory sandwiches made with homemade jam and/or peanut butter. Or head a couple trucks down to indulge in the Poutine fries at Potato Champion.

PBJ | 12th & Hawthrone, Portland OR | Map | WEBSITE
Potato Champion | 1207 SE Hawthorne Blvd, Portland, OR | Map | WEBSITE

Book a Tour > Portland Food Cart Walking Tour

7. 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. {photo}

Related Article: Do a Liquor Tasting at a Portland Distillery

Multiple Portland Locations | Map | WEBSITE

8. 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.

Multiple Locations | Map | WEBSIT

9. See 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. {photo}

Multiple Locations | Locations | Schedule | WEBSITE

10. Try the World-Famous Fish Sauce 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

3226 SE Division St, Portland, OR | Map | WEBSITE

11. Stroll Through 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 (see #5), so visiting both in one day is possible.

611 SW Kingston Ave, Portland, OR | Map | WEBSITE

12. Drink Liquor in Detention

McMenamins Kennedy School is an old elementary school turned into an entertainment haven. You can sleep in one of their guestrooms, 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.  {photo}

5736 N.E. 33rd Ave., Portland, OR | Map | WEBSITE

13. 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.

It’s a bucket list bonus if you get a hole in one.

509 Sw Taylor St., Portland, Oregon | Map | WEBSITE

14. 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. If 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.

Mount Hood National Forest | Map | WEBSITE

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

15. 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 Article: Have an Adventurous Meal of Pigeon, Heart & Cheeks

738 E Burnside St, Portland, OR 97214 | Map | WEBSITE

16. Eat a Voodoo Doughnut

I will admit that the base of these donuts 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 (see #3).

Related Article: Eat the Old Dirty Bastard at Voodoo Doughnut

Original Location: 22 SW 3rd Ave, Portland, OR | Map | WEBSITE

17. 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.

1626 NW Thurman St, Portland, OR | Map | WEBSITE

18. 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.

Monday – Saturday at 3PM | 100 SE Salmon Street, Portland, OR | Map | WEBSITE

19. Get Lost in Powells 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 Powells 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. {photo}

1005 W Burnside St., Portland, OR | Map | WEBSITE

20. 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.

11 SW 3rd Ave., Portland, OR | Map | WEBSITE

. . . Read More . .

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