Portland Bucket List: 45 Quirky & Fun Things to Do in Oregon’s Weirdest City

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


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!

Annette White at Starks Vacuum Museum in Portland Oregon

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.

The Smallest Park in the World in Portland, Oregon

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!

Pose under the Keep Portland Weird Sign

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.

The Witches Castle at Forest Park

Annette White at Forest Park in Portland, Oregon

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

International Rose Test Garden in Portland   International Rose Test Garden in PortlandInternational Rose Test Garden in Portland

2. ✦ 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 for hours for the images to develop and it will be dripping wet when it shoots out of the booth. It is quite an experience like no other. Do you feel like taking a journey back in time? 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.

Roller Derby at the Rose City Roller Portland{photo credit}

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.

Japanese Garden Portland in Portland, Oregon

21. ✧ Walk in the Redwood Grove at Hoyt Arboretum

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.

Detention Bar at Kennedy School in Portland
photo credit

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

Multnomah Falls Portland  Multnomah Falls Portland

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.


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!

Eat a Bug Sundae - Bucket List Things to do in Portland

Annette White eating a Bug Sundae at Freakybuttrue Peculiarium in Portland

29. ✦ 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.

It’s probably just easier to book a tour > Portland Food Cart Walking Tour

PBJ Food Truck in Portland, Oregon

Potato Champion Food Truck in Portland

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

Drink at a Distillery - Things to do in Portland
photo credit

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.

Eat Dirty Fries at Lardo - Portland Bucket List

33. ✦ Eat the Biscuits at Pine State Biscuits

Things to do in Portland: Eat 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

Eat Famous Fish Sauce Wings - Portland Things to Do

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

Eat Pigeon at Le Pigeon in Portland

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.

Tea Tasting - Bucket List Things to do in Portland, Oregon

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

Eat a Voodoo Doughnut - Portland Bucket List

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.

Portland Bucket List: Fun Things to See, Do & Eat in Oregon's Weirdest City | Activities, Attractions and Restaurants


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




2017-12-06T11:19:44+00:00 December 5th, 2017|Categories: BUCKET LISTS, North America, Oregon, TRAVEL|Tags: , , |

40 Comments

  1. Renuka September 24, 2014 at 11:30 am - Reply

    Portland is seriously amazing! So many things to do.

  2. Ryan Biddulph September 24, 2014 at 9:47 pm - Reply

    Hi Annette,

    LOL on 1.

    Have you seen Portlandia? Awesome show, funny as heck, and 1, as well as a few items on this list are consistent with the show’s take on the city.

    Portland seems so off the wall, funny, intriguing and just a change up from any city on earth. We’ve seen some pretty wild spots from growing up 30 minutes from NYC, to frequently hitting Bangkok, to Phnom Penh, etc, etc….and Portland seems like it’d be right up there for a spot to see.

    The food scene looks awesome.

    I’d have at those dirty fries in a minute because here in Fiji the fare is not up to snuff compared to Thailand and other places we’ve hit over the past 40 months. Dying to get at those dirty fries….oh well, back home in NJ for Christmas so we’ll have whatever we want, food-wise.

    Thanks much Annette way cool read.

    I’ll tweet this one to my travel blogger buddies in a bit.

    Ryan

    • Annette White September 25, 2014 at 6:18 am - Reply

      So funny, but as I was reading this comment I was watching Portlandia reruns because I’d never seen it!
      The food scene in Portland is ridiculously good and a large reason it’s one of my favorite cities in the world. The laid back vibe and quirkiness is also I huge factor.

      I’ve never been to Figi, but Thailand has incredible food too. Hope you get fries soon!

  3. Dane Homenick September 25, 2014 at 1:07 pm - Reply

    I can’t wait to hit up Portland. Thanks for the list!

  4. rebecca September 25, 2014 at 11:29 pm - Reply

    sooo much to do! dirty fries is one I really want to try

  5. Emma September 26, 2014 at 1:56 am - Reply

    So many great ideas. Don’t think I’ll be going for the insect sundae, though!

    • Annette White September 26, 2014 at 7:28 am - Reply

      I understand. But, still visit the Freakybuttrue Peculiarium because it’s not just about the bugs 🙂

  6. `Kerry September 26, 2014 at 8:54 am - Reply

    MMMMMM. Doughnuts, coffee, and books. 🙂 I love bookstores and have a goal of visiting bookstores all over the world.

  7. Stan September 30, 2014 at 11:29 pm - Reply

    That’s absolutely great glow in the dark miniature golf- such a fun place

  8. birmingham Taxi October 1, 2014 at 12:26 am - Reply

    Have you seen Portlandia? Awesome show, funny as heck, and 1, as well as a few items on this list are consistent with the show’s take on the city.

  9. Adam Sommer October 1, 2014 at 7:19 pm - Reply

    The worlds smallest park is hilarious! I actually think Id have to see that on my upcoming Portland trip!

    • Annette White October 2, 2014 at 10:33 am - Reply

      It is the cutest little thing! It’s worth a quick visit. Have fun in Portland 🙂

  10. […] 20 Bucket List Things to Do in PORTLAND | Bucket List Journey […]

  11. […] Annette White Portland is the largest city in Oregon and filled with quirky things to do that range from […]

  12. Mary Bolton October 26, 2014 at 10:30 pm - Reply

    My sons live in Porltland and with two of my gradsons! At one time they were working at The Bagdad and The Kennedy School! One worked at Powell’s too! Now one has a design company and the other works for him. Check out Murmur Creative! I live in Santa Cruz, CA…but I am in Maui right now! Found your site through Pinterest!

  13. […] when he strongly recommended we go to Dean’s Scene. With all of my hours of ‘things to do in Portland, Oregon” research this name escaped me. What? Where? He continued to give us a lengthy […]

  14. […] Want more ideas unique things to do in Portland? Read 20 Bucket List Things to Do in Portland. […]

  15. Courtney Sambuceto November 21, 2015 at 7:58 pm - Reply

    WOW! I was honestly really happy to find this very well put together post! I have traveled all over the country and Oregon in general is one of my favorite places…thank goodness I live here :)~ For those that haven’t been through Portland, WHAT ARE YOU THINKING?? Thank you for posting this, I truly appreciated it. FYI – I, like you, LOVE sharing this beautiful state, and everything there is to enjoy about Oregon. I have created a really awesome Resource Guide that took me quite a bit of effort and thought to put together. I am sharing it with anyone that wants to either get “Discover” or simply “Broaden” their Oregon Horizons!! I would love it if you could continue to share this with YOUR followers 😉 I am always looking to expand my own blog, and if you would like to share more of your postings with MY followers, please don’t hesitate to contact me.

  16. Mathew April 21, 2016 at 4:22 pm - Reply

    Nice list! This was a big help in planning our trip!

    • Annette White April 22, 2016 at 4:59 pm - Reply

      Thanks! Hope you have a great time and have some Pok Pok wings for me!

  17. Jason April 30, 2017 at 2:53 pm - Reply

    Super dope list of things to do. I’m visiting Portland soon and will be doing many of the things you suggested.

  18. Kalei May 22, 2017 at 4:27 pm - Reply

    Do you have a list (Part Deux, perhaps) for a Portland local that has done all of the things on this list, but wants to continue to explore the city? For example, one could be going to the Ping Pong bar, or other things that are more local like that. Let me know what you think!

  19. Jessica Zeigler August 11, 2017 at 8:52 am - Reply

    I’ve lived in Portland all my life and I’m still using your list to play “tourist” today. You touched on many of the gems. Thanks for loving my city.

    • Annette White August 14, 2017 at 6:19 am - Reply

      That means a lot coming from someone from Portland! I love your city 🙂

  20. Jenna Campo September 14, 2017 at 10:41 pm - Reply

    As someone actually from Portland, a lot of these things are way more hype than anything else, and many of them are common things that can be found all over. Portland is not like an episode of Portlandia where everything is beautiful and perfect and so fun and quirky… There is a massive homeless camping problem, with the associated crime with theft, assault, and break-ins. There is gang activity still prevalent and common. You don’t need to travel to Portland to look at roses, eat a doughnut, eat fries, eat hot wings, or drink tea. Just really obnoxious all of the tourism and television hype of Portland. It’s now becoming exceedingly overcrowded and they are tearing out all these “novelties” because so many of you tourists decide to move here: thus they tear out mom and pop shops, bowling alleys, quirky vegan shops, etc. just to make way for high rise apartment buildings. Most of these things are not unique to Portland, and in fact the cool things about Portland that actually are unique are ruined by tourism.

  21. […] Portland(Things to do Portland) […]

  22. […] Portland(Things to do Portland) […]

  23. Jade D'sa December 7, 2017 at 9:20 am - Reply

    Such unique things to do! Naked bike ride – whaaaaat?

    • Annette White December 7, 2017 at 10:46 pm - Reply

      It’s true! Probably would be one of the craziest events to see.

  24. Paulina Gaitan December 12, 2017 at 6:10 am - Reply

    Portland is a amazing city. This is one of my favourite cities in the world. Superb dope list of things to do. I’m visiting Portland soon and will be doing many of the things.

  25. Veronica Cavanaugh December 13, 2017 at 9:28 am - Reply

    I get around to the Portland area about once a year, so I really appreciate the unique list! McMenamins Kennedy School is a definite must next time.

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