Keep Portland Weird: Five Crazy Things to Do in Portland, Oregon

By Hope Nardini

Portland is plastered with “Keep Portland Weird” bumper stickers, t-shirts, and even billboards. It’s one of my favorite cities to visit, because there is always something strange and crazy right around the corner. From “zoo bombing” on kiddie bikes to setting your taste buds on fire with habanero cheese fritters, Portland will not disappoint even the most reckless daredevil.

Keep Portland Weird
Photo credit: Gwyn Fisher

Woodstock Mystery Hole

When’s the last time you shimmied down a mysterious hole in the ground suspected to contain artifacts from an ancient civilization? The Betz floods swept the Northwest after the ice age, and sediment buried the land under layers of hardened rock. The mystery hole is like a telescope into the past. When a family discovered it in their backyard blackberry bushes, they were shocked to find such rock formations as the Giant Double Arch and the Gaping Tunnel. You’ll have to sign a waiver, but you too can experience this strange discovery. The Woodstock mystery hole is just two miles west of I-205, and you can find out more information at

See Dead People

How do you feel about walking through seven miles of creepy hallway and chilly basement? Would you be even more spooked if you were walking among the dead? Although the Portland Memorial Mausoleum is now closed to the public, they do have special tour days periodically. You’ll see old Victorian architecture, crypts, urns, and notes left for the deceased. As you descend in the mausoleum, the place gets colder and creepier. Can you handle the mausoleum? There’s only one way to find out. The Portland Memorial Mausoleum is on 6631 SE 14th, and you can call  503-236-4141 to find out their next public tour date. Check for more information.

Run Barefoot…and Naked!

Portland is not a city for the conservatively clothed. There are barefoot, clothes-optional races available in Portland year-round. Barefoot running has been a developing trend since many runners claim they are more alert and build stronger leg muscles without footwear. In Portland, some runners take this trend to an extreme and forgo any athletic wear at all. Barefoot Beach Runs, in particular, are about four miles of sand trails along the Colombia River. 

Go Zoo Bombing

Keep Portland Weird
Photo credit: Barjack / Keary O

Don’t worry, zoo bombing doesn’t actually involve bombs. Rather, zoo bombers are adults and adolescents who race each other on kiddie bicycles (and sometimes tricycles) down the hills next to the Oregon Zoo. They go pretty fast, which means scrapes and bruises are common. It’s one of the most dangerous things to do in the city, and some kids get seriously hurt. The regular zoo bombers leave a pile of minibikes at their meeting point in front of 13th Street and Burnside. The group meets every Sunday at 8:30 pm. If you’re up for the challenge, you can find more information at

Great Balls of Fire

If you think jalapeno fritters need a little more kick, you have to try Salvador Molly’s Great Balls of Fire. These habanero cheese fritters are served with several glasses of water. They were originally created for Oregon Heat, a Portland non-profit organization that helps raise money for low-income residents having trouble paying off their heating bill. If you can stand the heat, you will be added to the Hall of Flame. Salvador Molly’s is located at 1523 SW Sunset Blvd, and is open seven days a week. 

Portland is a thriving city with a laid-back attitude. Next time you’re in the area, bring out your adventurous side and keep Portland weird with these five crazy activities.

Traveling to Portland? Find great deals on Portland accommodation here.


Hope Nardini is a Connecticut native who is currently bouncing around in the Andes. She has traveled to over 20 different countries, but she fell in love with South America after studying abroad in Buenos Aires. Nardini did research on immigration policy in Quito, Ecuador this summer and will be interning in Peru with an educational development non-profit this fall. When she’s not haggling at South American markets or dipping her hands in a jar of dulce de leche, Hope enjoys playing ultimate Frisbee, watching documentaries, and looking for the next big adventure.

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10 thoughts on “Keep Portland Weird: Five Crazy Things to Do in Portland, Oregon”

  1. LOVE this post! You hooked me from the get go with that outrageous nude biking photo. I’d love to see Portland’s “barefoot, clothes-optional races” but I’m not ready to participate… yet.

  2. Pingback: Your Guide to Not-so-weird Portland, Oregon | GoMad Nomad Travel Mag

    1. Well, we do have a pretty cool zoo, and Saturday Market is definitely not a bad place to check out. The Rose Garden (specifically, the International Rose Test Garden) is a nice walk and gives you a great view of the city; it’s also next to the Japanese Gardens. The Chinese Classical Gardens are downtown. Pittock Mansion is a nice visit. The Portland Art Museum and the Oregon Historical Society Museum are downtown; OMSI is fun for the younger kids (and maybe the older ones too). One more…a nice drive to Multnomah Falls is worth it…or Mt. St. Helens…or anywhere on the Oregon Coast…if you need a bike ride, riding downtown at Waterfront Park, the Marine Drive bike path, or the Springwater Trail offers a few possibilities. So there’s more than ten NOT so weird suggestions from a Portlander who could care less about the massively over-hyped “weird”ness that not everyone subscribes to.

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  4. Thanks for letting out our secret,lol. We love our town and all the wonderful and weird things and people here. You should also have mentioned Portland Saturday Market which is actually on sat. and Sun. Great things to buy from local artisans and good food. There are also a mix of street performers including one Jimmy Hendrix look alike.
    Come one come all but be prepared for the rain in the spring and all fall and winter.

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  7. Pingback: Portlanders Ranked 4th for Strangest People in Nation | Just Out

  8. Peter Korchnak

    Even as a 14-year Portland resident for the longest time I didn’t even know the Woodstock Mystery Hole existed. Not sure if it’s open anymore, either. There’s so much weird to explore in Portland I compiled a list of 365 such things and I’m still growing the list…

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