“Keep Portland Weird” has become Portland, Oregon’s unofficial battle cry. Originally intended to help promote local businesses, the slogan soon found its way into the wide array of catchphrases (and bumper stickers!) and fueled the fire of everything that makes Portland amazingly unique.

If you’re planning a trip to the Rose City and simply looking for a few “out of the box” activities in the area, here are a few weird things to do in Portland that will definitely make an impression!

The Alibi Tiki Lounge

Alibi Tiki Lounge | Photo courtesy of Rob S.

Established in 1947, this Portland institution has been a part of the city’s unique character for centuries, initially as horse drawn carriage stop in the late 1800s as the Chat-n-Nibble. Now you can spot the grand neon sign from a distance, luring patrons in for tall frozen drinks and an endless list of karaoke favorites. The bar’s tropical decor offers a welcome respite from quintessentially gray Portland days.

The World’s Smallest Public Park

Mill Ends Park
Mill Ends Park | Photo courtesy of Piutus

Pack a picnic basket and stretch out in the expansive 452-square-inch field at Mill Ends Park. This lush garden park is located in the median of the perpetually busy Natio Parkway near SW Taylor Street in downtown Portland. The park was conceived by journalist Dick Fagan in 1946 after noticing a hole meant for a light pole beneath his second story window. The light pole was never installed, and as the area began to become overgrown with weeds, he took matters into his own hands, planted flowers, and named the park after his newspaper column, “Mill Ends.”

VooDoo Doughnut

The Voodoo doughnut
The Voodoo doughnut | Photo courtesy of R. Crap Mariner

When VooDoo Doughnut first opened, employees left the small bakery in the early morning hours to scour the streets for musicians and barflies, and handed out doughnuts covered in crushed-up headache medicine with a shot of antacid sitting in the center. This evolved into the highly sought-after, wacky flavor combinations fans have come to love, from bacon maple to Cap’n Crunch.


Weird Things to Do in Portland - Peculiarium
Peculiarium | Photo courtesy of Hello Chaos

Featuring one-of-a-kind attractions and exhibitions, the Peculiarium follows its motto to a T: FreakyButTrue. Stepping into the spotlight on CNN and several travel TV shows, this emporium showcases oddities that range from depictions of alien experiments to hair-raising tales of Big Foot encounters. Calm your nerves with one of their signature ice cream sundaes afterwards as you reflect on the X-Files-style experience.

Goodwill Outlet—AKA “The Bins”

The Bins | Photo courtesy of longan drink

Okay, so this one technically isn’t in Portland: but Milwaukie is just a 15-minute drive from downtown. You won’t want to miss this one if you’re on the prowl for a great thrift shop find. A regular stop for bargain hunters and vintage enthusiasts, it’s Black Friday every day at this Goodwill Outlet. Goodwill Industries of Columbia Willamette processes roughly 106140 TONS of donations a year, which is where this thrifter’s dream comes in. Sift through countless bins of electronics, clothing, oddities, and other treasures for sale at rock-bottom prices. After one visit, you’ll find yourself coming again and again, looking for the next deal of the century.

Shanghai Tunnels

The Shanghai Tunnels
The Shanghai Tunnels | Photo courtesy of Keary O.

History buffs will not want to miss out on a trip to the historic Shanghai Tunnels. Shrouded in tall tales, dark secrets, and claims of hauntings, these tunnels play host to tours that take you through less-than-savory moments in the city’s history. Learn the truths (and gross exaggerations) that have made these tunnels both famous and infamous.

PDX Adult Soapbox Derby

adult soap box derby portland
Portland Adult Soapbox Derby | Photo courtesy of Kurt Ehnle

Take your love of racing video games and mingle it with the nostalgia of soap box derbies with the Portland Adult Soap Box Derby. Held at the end of August every year, this event brings dreamers, engineers, and daredevils into the same arena and sends them flying down the hills around Mt. Tabor Park. Bolstering camaraderie through teamwork, science, and a bit of silliness, this is an event you won’t soon forget!

Kidd’s Toy Museum

Kidd's Toy Museum
Kidd’s Toy Museum | Photo courtesy of Chris R.

Enter the magical age before plastics at Kidd’s Toy Museum. This colossal toy museum appeals to both children and children at heart and features one of the finest collections of antique mechanical banks and die-cast toys in existence. Ambient, dim lighting combined with wall-to-ceiling curiosities are a children’s fantasy book come alive.

Portland Saturday Market

Portland Saturday Market
Portland Saturday Market | Photo courtesy of Susan Smith

While it may not be weird or “out of the box,” the Portland Saturday Market is the perfect place to see the melting pot of cultures and beliefs that make the city great. Grab a sugar-covered elephant ear while you sip a local brew and check out the local woodworking artists and glass blowers. If you’re lucky, you might catch a glimpse of the unicycle-riding Darth Vader playing his fire-spouting bagpipes. Now if that isn’t unique, we don’t know what is!

World Naked Bike Ride

portland naked bike ride
World Naked Bike Ride | Photo courtesy of Sam Beebe

Not for the faint of heart, Portland plays host to the World Naked Bike Ride. Started in 2004, this is the local piece of a world-wide puzzle that promotes everything from a greener, cleaner planet to self-acceptance and a healthy body image. No matter how or why you ride, you must remember only one thing: Bare as you dare.

These events, venues, and attractions are just a small sampling of weird things to do in Portland. Our recommendation? Just walking around! A journey on foot lets you explore at your own pace, where you might encounter a quirky bookstore or farmers market. And who knows—you might just encounter Portland’s very own bagpipe-playing, unicycle-riding Darth Vader (yes, really). No matter what, a trip to Portland is guaranteed to be filled with a healthy dose of oddity.

Feature photo courtesy of Sarah Kidd

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Author: Ryan Stevens

Ryan’s love of boutique wines and small batch brews has fueled his writings and travels. Sharing local secrets is his specialty, from taking travelers to the hidden vineyards and gems of the Willamette Valley to showcasing the best spots to pop in and grab a pint in San Diego.