Portland is celebrated for its food and a vibrant creative culture. But it’s also celebrated for being weird. Dig deep and you’ll find a treasure trove of the unusual and the unique. For adventurers looking beyond the conventional tourist trails, Portland offers a plethora of odd and intriguing activities to explore.

In my two decades in Portland, I’ve lived in a number of different quirky neighborhoods. Each one has its own ‘small town’ feel and each embodies a unique spirit of individuality. A place where the residents are free to express themselves without judgement. You’ll find part of this expression in the way they decorate their houses and yards.

Whether you are just visiting Portland or have been a local for years, I encourage you to carve out an entire day to checkout all of the unusual things to do in Portland that make it, well…Portland!

Weird Things to Do in Portland

The Sidewalk Joy Map

An innovative community project known as the Sidewalk Joy Map is transforming the way residents and visitors explore the city’s vibrant neighborhoods. It’s a creative initiative that maps out routes highlighting not just the most direct paths, but those that offer the greatest joy! Here you’ll find elements of natural beauty, art, and quirky landmarks.

It encourages people to slow down and appreciate the small wonders of urban life, from hidden gardens and street art to whimsical decor and community spaces. The Sidewalk Joy Map exemplifies Portland’s spirit of community and its residents’ appreciation for the little things that make everyday life more delightful.

Freakybuttrue Peculiarium

One famous curiosity in town is the Peculiarium, a museum/gallery/store in Northwest Portland that is as bizarre as its name suggests. Inside, visitors can immerse themselves in interactive exhibits featuring alien autopsies, creepy dolls, and a range of oddities that teeter between the intriguingly grotesque and hilariously bizarre. It’s a perfect encapsulation of Portland’s celebrated motto, “Keep Portland Weird.”

Witch’s Castle in Forest Park

Not far from the urban buzz is the Witch’s Castle, nestled in the verdant expanse of Forest Park, one of the country’s largest urban parks. This isn’t your traditional castle; rather, it’s the ruins of a stone structure ensconced in moss and local lore. The Witch’s Castle has a storied past of family feuds and eerie legends, making it a fascinating, if slightly spooky, hiking destination.

To get to it, hike the Lower Macleay Trail in Forest Park. It is an easy hike with a small amount of elevation, about a mile from the trailhead. A very pretty hike and one I go on often.

Portlandia Statue

The Portlandia Statue is the second largest copper statue in the U.S., second only to the Statue of Liberty! You’ll find it in downtown, smack dab in front of the Michael Graves Portland Building. It is a woman in classic Roman garb holding a trident. Some have described the statue as downright creepy. But it cannot be denied that it is striking – and a jarring sight when viewed with the rest of the scenery.

Morrison Street Mini Gallery

This is part of the PDX sidewalk joy initiative, but deserves its own shout out because it’s just so dang cute. With an ever-changing display, the mini gallery is housed in one of those mini library boxes that you’ll find scattered in neighborhoods throughout Portland. This is a must-stop on your unusual places in Portland tour.

If you are a regular visitor to Portland or a resident, be sure to check it out every few weeks for a different display! It’s easy to find, just type ‘Morrison Street Mini Gallery’ on your GPS.

The Vacuum Cleaner Museum

Stark’s Vacuum Cleaner Museum stands as a testament to Portland’s knack for the quirky. This offbeat museum showcases vintage vacuum cleaners, offering insight into the evolution of household technology. It’s a quirky, yet surprisingly fascinating, glimpse into the history of everyday appliances, reflecting Portland’s culture of celebrating the unconventional.

Shanghai Tunnels

Lastly, for those who relish in the city’s underground scene—literally—the Shanghai Tunnels or Portland Underground offer a stark glimpse into a darker chapter of Portland’s history These underground passages, once used for the illicit practice of shanghaiing, are rumored to be haunted. Guided tours recount tales of ghosts and unsavory characters from Portland’s past, providing a chillingly unique historical perspective.

Book this tour to the Shainghai Tunnels here!

Zymoglyphic Museum

Exploring Portland further unveils more eccentric gems hidden within its streets and landscapes. The Portland Zymoglyphic Museum, showcases the art and beauty of decay through a collection of natural and crafted curiosities, aiming to present a unique perspective on the lifecycle of nature. It’s a must-see for those interested in the intersection of art, nature, and the ephemeral. Be sure to check out their website for opening hours, as they tend to be limited.

Mill Ends Park

In the heart of Portland lies Mill Ends Park, officially the world’s smallest park according to the Guinness Book of World Records. Spanning a mere two feet across, this diminutive green space is a whimsical testament to the city’s love for the quirky and unusual, hosting miniature events and serving as a humorous point of interest.

It lies in the middle of a busy intersection very close to the river in downtown Portland. You may even see it decked out in various states of cheer, if you’re lucky.

The Troll Bridge

Travel just a short way north of town and seek out this whimsical bridge that has become a pilgrimage for the funky and the curious. The bridge and its surroundings are adorned with troll figurines and paintings, creating a captivatingly eerie yet fascinating scene straight out of a fairy tale.

Bring your own plastic trolls and add to the fun. You can find the bridge on your GPS if you simply type ‘Troll Bridge.’

Rimsky-Korsakoffee House

Operating in an old house that seemingly defies the ordinary (read: haunted), this coffee shop offers a cozy atmosphere with which to indulge in some sweet treats. With its rotating tables and occasional live classical music, the Rimsky-Korsakoffee House serves up a unique experience along with its coffee and desserts.

Their coffee is so-so (but hey, I’m a coffee snob, so…) but their desserts are amazing and always changing, with a few mainstays. Plan accordingly because they don’t open until 7pm and are open until midnight. Bring your cash! Because they don’t take any other form of payment.

Read about my experience here.

Drink a Beer at School

This isn’t your typical school. The McMenamins Kennedy School is a historic schoolhouse that has been transformed into a hotel, complete with several bars, a restaurant, a movie theater, and a soaking pool. One of the bars is even called Detention Bar. The hallways of this urban resort are filled with artworks and photographs that tell its century-old history.

Read about my love for the McMenamins franchise here.

Book your stay at McMenamins Kennedy School here.

The Weather Machine at Pioneer Courthouse Square

A peculiar piece of public art that predicts the weather. At noon each day, the Weather Machine announces the next day’s forecast in a rather dramatic fashion, featuring a mist-spewing dragon for rain, a golden sun for clear skies, and a blue heron for overcast days.

Right next to the weather machine, look for a circle in the bricks on the ground. Stand directly on this circle and face the Starbucks, then start talking. You’ll experience a weird echo that is a phenomenon caused by the unusual acoustics in this area of Pioneer Courthouse Square.

The Wishing Tree

Nestled in a quiet North Portland neighborhood, this tree has become a communal spot for people to share their deepest wishes. Visitors hang their wishes written on tags, creating a colorful and moving tapestry that reflects the hopes and dreams of the community.

The UFO at Collins Beach

Yes, you read that right. On the serene sands of Collins Beach on Sauvie Island lies a homemade UFO, a peculiar sight that has intrigued beachgoers and sparked the imagination of many. It’s a testament to Portland’s love for the strange and the unexplained.

Hippo Hardware

More than just a hardware store, Hippo Hardware is an emporium of the weird and wonderful. From vintage lighting fixtures to rare plumbing parts, it’s a treasure trove for anyone looking to add character to their home. The exterior of the building, located on the busy East Burnside Street, is adorned with Romanesque-painted columns and, you guessed it, hippos.

The Unipiper

Lastly, The Unipiper is an individual rather than a place, a quirky guy who is Portland’s mascot of sorts, embodying the city’s eccentric soul. Often spotted on city streets riding a unicycle and donning a Darth Vader mask while playing bagpipes, The Unipiper has become a local superhero, symbolizing Portland’s enduring love for the whimsical and bizarre.

These attractions barely scratch the surface of what Portland has to offer to those willing to stray from the beaten path. Each visit reveals more layers to the city’s eccentric charm, ensuring that even the most unusual preferences are catered to. It’s why I love this city like no other, and why I’m proud to call it home.