Keep Portland Weird: 7 Must-Dos for Your PNW Bucket List

‘Keep Portland Weird’ isn't just a catchy phrase—it's a way of life. Beyond fancy donuts, famous airport carpet, and stunning natural beauty, the City of Roses offers a plethora of experiences that embrace the wackier side of life. Ready to ditch the mainstream and check off some truly unique adventures from your Oregon bucket list? Your Instagram feed (and your memories) will thank you!

The Witch's Castle

Shrouded in moss and legend, a hike into the heart of Forest Park leads to the creepily captivating Witch's Castle. This enigmatic stone structure is a mysterious remnant of Portland's past, with wild stories about its origins—including a tale of murder and star-crossed lovers. The land became a park in the 1930s, before the building was damaged during a heavy storm and abandoned—only to become a popular party spot for Portland teens in the 1980s. Nestled in the dense forest near downtown, it’s a great hike for anyone who, like Lydia Deetz, prefers the “strange and unusual.” 

Next Level Pinball Museum

No trip to the Portland area is complete without a visit to the award-winning Next Level Pinball Museum in Hillsboro, which has held the title of "World's Favorite Pinball Arcade" for three years running. With over 600 games on free play, you'll find classic favorites alongside modern machines, spanning decades of the game’s evolution. This huge haven isn't just about pinball, though—it's a pop-culture extravaganza featuring an extensive lunchbox collection, iconic movie memorabilia, and a treasure trove of vintage toys. It's a day full of fun for all ages, a true gem for pinball enthusiasts, and a quirky adventure for anyone seeking a dose of retro entertainment.

Oregon Vortex

Add a touch of mystery to your trip with a visit to the Oregon Vortex, a roadside attraction since 1930. Self-described as “an area of naturally occurring visual and perceptual phenomena which can be captured on film,” the vortex is said to make objects defy gravity and other laws of nature: balls roll uphill, brooms stand upright, and people appear dramatically taller or shorter as they switch places. It was even featured on an episode of “The X-Files” in 1999! Come explore the House of Mystery and enjoy a classic taste of Americana buried in the lush greenery near the southern border of Umpqua National Forest.

Ole Bolle at Nordic Northwest

For a whimsical encounter inspired by Scandinavian folklore, add a stop at Ole Bolle to your itinerary. Created by artist Thomas Dambo, the giant troll sculpture bends to peer into a small red cabin, searching for a treat (or a little mischief!). Made from recycled wood pallets, Ole Bolle is one of six hand-built trolls installed by the Danish sculptor across the PNW, and the only one in Oregon. This public art installation is a delightful detour for families and anyone who loves Scandinavian culture—but you might want to bring some cookies to feed the troll!

The Wreck of the Peter Iredale

For history buffs, a visit to the Wreck of the Peter Iredale is a must. This four-masted steel barque met its fate in 1906, succumbing to high winds on the Oregon Coast before running aground and snapping three masts. All 27 people on board, including two stowaways, were rescued by a team from Point Adams. Now a permanent resident of Fort Stevens State Park, the skeletal remains of this once-mighty ship jut from the sand, a sobering reminder of the awesome power of nature and an iconic piece of Oregon's maritime past.

Portland Troll Bridge

If you’ve always preferred the ogre to the prince, head to the Portland Troll Bridge for a whimsical encounter on the outskirts of town. Tucked away in a fern-draped forest, this unassuming railroad trestle has been transformed into a quirky art installation as locals add a colony of little troll dolls to its wooden planks. To get to the trolls’ enclave, head northwest out of Portland on NW St Helens Road, then take a left along McNamee Road and you’ll soon reach the bridge. Don’t forget to bring a troll!

PDX Adult Soapbox Derby

Inject some adrenaline into your Northwest adventure with the PDX Adult Soapbox Derby. Every August, this free tournament—called “the best event in Portland”—transforms Mt. Tabor Park into a riotous racetrack. Witness the ultimate DIY showdown as teams hurtle down a closed course in their handcrafted soapbox racers. But speed isn't the only factor—creativity is king! You’ll see wacky car designs, outrageous costumes, and a supportive crowd cheering on the racers. It's a fantastic display of the playful spirit Portland is known for, and a perfect way to experience the city's vibrant community.

Have we inspired you to explore our fair state? Stop by for a visit while you’re here, or get a look at what’s in store for the future.