Portland, Oregon prides itself on being weird and unusual – just take a look at the cars and you’re bound to see a “Keep Portland Weird” sticker. If you’re planning to visit Portland, add a few of these places to your itinerary to get the full Portland experience.

Unique ideas for a Portland Vacation

Starks Vacuum Museum

The Starks have been selling vacuums in Portland since 1932. In addition to their little shop, their museum with more than 300 models of vacuums is one of the top places to visit in Portland.

Naked Bike Ride

Thousands of people gather in Portland every summer to participate in the Naked Bike Ride. Even if it’s not something you want to participate in, it’s definitely one of the more unusual things to experience in Portland.

The Witch’s Castle

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Despite its name, The Witch’s Castle has no ties to witchcraft. Students who liked to throw parties at the ruins gave the site its nickname. The ruins are nearly 100 years old and provide a nice hike through the woods. You can learn the real and tragic story behind the property along the way.

Freakybuttrue Peculiarium 

When you visit Portland, be sure to stop at the Freakybuttrue Peculiarium where admission is free and there are more than enough oddities to go around. Enjoy a sundae topped with real bug larvae while exploring the unusual exhibits.

The Hat Museum 

It’s no surprise that Portland is home to one of the largest hat collections in the country. Check out fashion trends through the ages as well as hats used for different jobs in generations past.

Mill Ends Park


Mill Ends Park sits in an area that covers just 452 square inches, making it the smallest park in the world. Dedicated in 1948, this little park is home to a tiny leprechaun.

Shanghai Tunnels

Those into the scary and unusual should check out the most haunted place in the country: Shanghai Tunnels. A network of kidnappers smuggled people through these tunnels, and it’s rumored that some visitors can hear their screams and moans during the tour.



What’s a trip to Portland without a healthy smoothie or juice? Visit Moberi for a refreshing drink. The catch is that you have to pedal a bike to power the blender that makes your beverage.

McMenamins Kennedy School

McMenamins Kennedy School used to be a fully functioning school, but now it’s a quirky hotel. Chalkboards, water fountains and other school features are still intact. Detention has even been turned into a bar.

Casa Diablo

Nothing quite sums up the essence of Portland like a vegan vampire-themed strip club. Though not suitable for kids, it’s the perfect place for adults to unwind and let loose.

Paul Bunyan Statue


The giant Paul Bunyan statue is one of the top places to visit in Portland. Smile at his goofy grin, and pose for a photo with the lumberjack.

Jetliner Home in the Woods

There are some unique vacation rentals in Portland, Oregon, but none of those homes compare to the Jetliner Home in the Woods. The 727 airplane turned dream home is just outside the city and visitors are welcome.