365 Weird Things to Do in Portland, Oregon

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  • A compendium of people, places, events, and things that make Portland, Oregon weird
  • Your companion for your visit to Portland, Oregon: Experience “Old Portland” to its fullest
  • 130 pages, 115 photos, 1 massive awesome
  • PDF, 14 MB
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The slogan “Keep Portland Weird” has become Oregon’s biggest city’s unofficial motto and mantra. Thanks to a slew of positive press and the TV show Portlandia, whose premise pegs Portland as the breeding ground for the strange and the unusual, people flock to Portland to bask in its weirdness. But what’s so weird about Portland, Oregon anyway? Tired from walking through a farmers market one day, we sat down over some pints of craft beer to compile this list of 365 weird things to do in Portland, Oregon—one for every day of the year!

The e-book 365 Weird Things to Do in Portland, Oregon showcases the bizarre and hilarious people, places, and things that keep Portland weird. Our recommendations focus on what makes Portland unique, like our small, independent businesses, and what makes it diverse, such as the people who work hard and play hard here.

eBook Download

The ebook ships in PDF format, viewable with Adobe Reader/Acrobat or native viewers on these platforms and devices:

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The ebook comes with five downloads (you can download it from the checkout page and confirmation email a total of 5 times). The download link expires in 180 days.


The ebook is divided into 6 sections:

  • Only in Portland
  • Food and drink
  • Events
  • Outdoors and wellness
  • Culture
  • Shopping

Weird things to do only in Portland

Locate painted cars

Car as canvas may not be a uniquely Portland thing, but most painted vehicles around Portland are Pacific Northwest-themed—and thus properly weird. Or are they just painterly projections by spirits suffusing the local woods? Either way, painted cars aren’t easy to spot (you have to get to the East Side) and the lucky sighting will likely be ephemeral—just like your time in the city.

Bust some asphalt

All that urban greenery in Portland didn’t just fall from the sky, it was made. One of the most inspiring contributors is the local nonprofit Depave, which works to transform paved areas into community greenspaces. Spend a day volunteering with them to truly connect with the local community—and build up some muscle.

Become a pinball wizard

Ground Kontrol to Major Tom: you will love to visit if you’re a nerd. The downtown video game arcade and after-5 bar has legendary status among the playing masses. Sixty classic and some new video games. Twenty-seven pinball machines. Regular events like Pinbrawl and Laser League. And trivia nights. DJs. Nostalgia. Beer.

Read sidewalk poems

The southern side of the 300 block of SW Yamhill is peppered with famous people’s quotes that read like poetic fragments. Slow down, read the 81 pavers on the sidewalk and plaques on walls designed by Portland’s own Katherine Dunn and Bill Will, and ponder: Who am I? What does it all mean? Is Portland really weird or is it all a computer simulation?

Take a selfie with Paul Bunyan

His statue that is. Parts of North Portland have that peculiar roadside attraction feel (shady motels on Interstate anyone?), and none other than the Paul Bunyan statue at the edge of the Kenton neighborhood. With peeling bunions from a botched repaint and a checkered shirt, the 31-foot attraction harkens back to the olden times before anyone even heard of weird Portland.

Weird things to do in Portland, Oregon: Food and drink

Sample Latin-American food at Mercado

Sometimes the government gets it right. The Portland Development Commission project in deep SE Portland, Mercado, hosts a slew of Hispanic stores, including a market, coffee shop, butcher’s counter, and a bar in a small mall-like building flanked by a plaza hosting a row of colorful food carts serving dishes from across Latin America. Portland Mercado is hands down one of the best places to go in Portland for Central and South American food and culture.

Eat some vegan comfort food

If you are thinking of going vegetarian, vegan, or just introducing more plant-based foods into your diet, Papa G’s Organic Vegan Deli is the place to check out for inspiration. There’s nachos, pizza, dogs, and burgers—and everything on the menu is completely vegan. Papa G’s reminds us being vegan doesn’t mean you have to give up the comfort food. They also make cashew yogurt and something called coconut kefir, in case those things sound appealing to you.

Sweeten your day in Little Havana

Little Havana is very little in Portland—the size of Pambiche Cosina & Repostería Cubana restaurant in NE, crammed with tiny tables and colorful paintings. The postres here cannot be beat. Pair one (our fave is the Guava Cheesecake) with Cafe Cubano, an espresso served with a stick of sugar cane.
Bonus: Get your taste buds ready with an epic, Cuban-themed mural covering the entire side of the building.

Visit a nanobrewery

The famous slogan’s knockoff, “Keep Portland Beered,” expresses the vigor of the local craft beer culture. Elevate your drinking game by visiting the smallest of the 70 breweries in town. Most nanobreweries don’t have taprooms, but Backpedal Brewing does (opt out of the Brewcycle, that’s just annoying).
Alternatives: Spring Nano Beer Fest in April or Fall Nano Pub Crawl in October.

Huddle around a bonfire

Portlanders, the renegades that we are, refuse to stay inside during the rainy, cold season (which lasts for most of the year). To mitigate the discomfort, bars compete for customers by building sprawling, covered, heated patios so Portland’s drinking masses can get tipsy in the fresh—don’t mind the cigarette smoke—air. Roadside Attraction is the rural barnyard-garage-sale-design version. They have a kickass fire pit, and the interior is pretty cozy too. Cash only.

Weird things to do in Portland, Oregon: Events

Look behind brewery curtains (February)

Dozens of breweries open their doors for guests during Zwickelmania for tastings, tours, beer and food pairings, meet-the-brewer haps, and more. Join the largest craft beer celebration in Oregon (yes, it’s statewide) on Presidents Day weekend.

Get as bare as you dare at Naked Bike Ride (June)

The most notorious Pedalpalooza event involves thousands of bicyclists riding around town in various stages of undress. The Naked Bike Ride is the biggest of the World Naked Bike Ride events and one of the weirdest free (in more ways than one) things to do in Portland.

Swim with goddesses (July)

On a splendid August night, “mere mortal women shed their suits and inhibitions and swim as Goddesses in the light of the full moon.” The Naked Goddess Swim celebrates both the female form and access to the Willamette River. Reservation required, women only (the event is trans-friendly).

Wash your dirty pooch for charity (September)

Don’t expect a bunch of busty, braided, beer-boot-slinging waitresses at Dogtoberfest. This festival, put on by Lucky Labrador Brewing Company, is a charity dog wash. The suds are not all for the dogs, though. The Lucky Lab brews its special Dogtober Festbier for the event, and the celebration includes food and live music.
Bring your pup for a spa day, enjoy a pint or two, and donate some money to Dove Lewis, a local animal hospital.

Ignore your mother’s warnings at Drag Queen Brunch (Sundays)

The smarty pants at Night Light Lounge hardly exaggerate when they say your mother warned you about shows like their Sunday Drag Queen Brunch. Ignore that voice and let your hair down at the only all ages and weekly daytime drag show. Portland generally takes its brunch seriously, except when there’s drag dance numbers, then it’s really on.

Weird things to do in Portland, Oregon: Outdoors and wellness

Spot a seal from the river bank

If Pioneer Courthouse Square is Portland’s living room, the Tom McCall Waterfront Park, colloquially known as the Waterfront, must be its back yard. Here’s where festivals take place come spring, here’s where downtown workers stroll or eat lunch on their breaks, here’s where bicyclists zoom to access points between Hawthorne and Steel Bridges and beyond.

And here’s where you can spot a lone seal poking its head out of the water as it floats in the Willamette River. If you’re lucky, that is.

Watch your little ones frolic in a fountain

A popular Pearl district fountain features a set of cascades filling a shallow pool, creating an ideal spot for small children to run around. And around and around the Jamison Square Park fountain on hot days they do—and yours can too.

Alternative: Fountain in the Waterfront Park at SW Salmon.

Pittock the fool at an old mansion

Pittock Mansion embodies Portland’s pioneer history at its grandest. The best (and free) part of the experience, however, is the journey to it. Dubbed “Portland hiking at its best” by the local rag once edited by Henry Pittock himself, the 5-mile (round trip) hike begins at Lower Macleay Park, under the NW Thurman Street bridge. The busy trail winds along Balch Creek, past an abandoned building nicknamed Witches Castle, and up through the magical Forest Park.

Stroll through a rhododendron grove

The Crystal Springs Rhododendron Garden belongs at the top of the list of Portland’s hidden gems. A sprawling network of trails through rhodie groves and ponds offers a serene getaway from the city’s bustle and one of the most romantic things to do in Portland, Oregon. Free from October to February and on Mondays otherwise.
Pair with a stroll around Eastmoreland mansions or Reed Lake.

Take a hike with the Mazamas

Members of Mazamas have been hiking and climbing around Oregon for more than 120 years. Explore the city (at quite a fast pace) on one of their Portland Street Rambles or join their out-of-town hikes via Meetup.com.

Weird things to do in Portland, Oregon: Culture

Hunt for Red October in a submarine

The U.S. Navy’s last non-nuclear attack submarine, USS Blueback, is permanently stationed in the Willamette River, just south of the Hawthorne Bridge, as an Oregon Museum of Science and Industry exhibit. Featured in the action movie The Hunt for Red October, there are daily and technical tours, the latter led by Navy veterans, and you can also sleep on the sub overnight.

Sean Connery would be shtoked.

Watch a cheap flick at a student cinema

Run by students and frequented by students and other cheapskates, the 5th Avenue Cinema is Portland’s only true proletariat art cinema and Oregon’s only student-run cinema. It’s $5 for the general public, $4 for students and seniors, and free for Portland State University students and faculty (with ID). There aren’t many cheap things to do in Portland where you’ll have the opportunity to torture yourself sitting through The Room on the big screen for such a low price.

See a foreign film

Part of the Portland Art Museum in downtown, NW Film Center organizes a ton of film-related activities around town. Visit the the Whitsell Auditorium, in February to see a foreign flick during the Portland International Film Festival or in May for a Czech film screened exclusively during Czech Film Festival. A little bit of Europe in the heart of Portland.

Weird things to do in Portland, Oregon: Shopping

Remember your birthday with a magazine

Yeah yeah, Powell’s blah blah. You really want to be at nearby Cameron Books and Magazines, established in 1938 (yes it is Portland’s oldest bookstore). Why? This is the only place where you’ll find a magazine from your birthday month and year (not guaranteed but you’ll definitely find a vintage Life or Playboy or pulp fiction mag issue to console you). Now with a new, Human Wildlife-proof gate!

Find treasures at a nonprofit art supply store

Someone’s dusty, frayed old pipe cleaners from a second-grade project are another person’s homage to the late, great Prince. This is the philosophy behind Scrap, a reuse store in downtown Portland that brings unwanted crafty items to the crafters who will put them to creative use. Prices are low, thanks to donations, and you’ll find anything from doll heads to yarn to clay to googly eyes. They even host classes called Crafternoons, where you can learn different ways to make stuff that will sit unpurchased on your Etsy site.

Get native plants

As you land or drive in to Portland and look out the window, you’ll see a sea of green. So. Many. Trees. Thank you, rain! If you are a gardener, you’ll surely want to take some of Portland’s greenery with you (don’t even think about the weed, we’re talking about plants). Head to Xera Plants in SE Portland to choose from a range of common and rare plants native to Western Oregon.

Portland: Come for the trees, leave with a tree (or a shrub or a grass).

Can’t decide, weirdo? Check out additional 99 of 365 things that make Portland weird.

3 reviews for 365 Weird Things to Do in Portland, Oregon

  1. Rebecca Schlessinger (verified owner)

    Longtime Portland residents Peter Korchnak and Lindsay Sauvé are connoisseurs of weird, which makes them the perfect guides to a city internationally renowned for its abundance of strange and quirky charm. They cover the classics for first-time visitors – Voodoo Donuts, themed bike rides – while also highlighting the off-the-beaten-path places and people that truly keep Portland weird. Where else will you find a guidebook that tells you where to go to “have velvet Amy Winehouse watch you eat fried chicken” or “pet a superhero pig”?

    As a fellow Portlander who lives for the tiny horses, parading mermaids, and unicycling Star Wars villains that can’t be found anywhere else on Earth, I must say y’all captured the spirit of our fair city quite well.

  2. Jen Shafer (verified owner)

    An amazing compilation of weird (and not-so-weird) things to do in my former town! I kept thinking, “oh, they forgot such-and-such,” only to run across “such-and-such” later in the e-book – it’s quite a comprehensive list! We’ve been gone since 2013 so I also noted many new things we need to do on our next visit.

    The best part was hearing Peter and Lindsay’s “voice” throughout the narrative… their style is engaging and entertaining. I’d encourage all Portland residents AND visitors to buy this book!

  3. Jeanne Sharpy (verified owner)

    If you live in Portland and think there is nothing to do on any day of the week…think again! If you are visiting Portland and want to explore what makes it special and get to the bottom of its weirdness……this is your guide! Who knew?!? Well…some of us had an inkling… but this gives you ideas you never would know unless you dive deep into this read! So sit down with a cup of coffee or a glass of beer and plan your day, weekend or year! Such a fun way to understand Portland and all it’s weird ways!

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