Adventures with Holly & Bryan

Some of Portland’s weirdness comes naturally. There are four volcanoes within city limits, for example, and thousands of birds dive into a school chimney on September evenings.

Other weird Portland things reflect the delightful weirdness of Portlanders themselves. It’s a place where pianos materialize in the city parks in summer, where contestants carve boats from giant pumpkins and paddle-race across a lake, and where if you’re lucky, you might just spot a unicycler wheeling down the street while playing bagpipes emitting streams of fire. 

In today’s post, I’ll share 13 weird things to do in Portland so you can experience the weirdness yourself. Let me know in the comments if you have other favorite weird things to do in Portland!

To be fair, a lot of Portland isn’t weird at all. From the tall hilltop park in my neighborhood, the city spreads out below like a landscape painting. Plump treetops in shades of green and gold bloom above the gridded streets down to the river, where the tall buildings of downtown rise skyward. The lights of cars and buses bob along on the roadways. It looks peaceful and orderly and ordinary. It’s when you look closer that the weird things in Portland begin to emerge.

So, what exactly are the weird things to do in Portland? Here are 13 top weird things to do in Portland to get you started.

1. Watch thousands of birds dive into a chimney at sunset.

There are plenty of high points around town to catch a breathtaking sunset, but if a weird sunset is what you’re after, head to Chapman Elementary on a September evening. You’ll find the grounds increasingly crammed with lawn chairs as sunset approaches, as hundreds of Portlanders gather to watch the nightly spectacle. If you look up, you’ll see that thousands of little birds called Vaux’s swifts are gathering, too. The swifts gather overhead, then circle, and then dive into the chimney just after sundown.

One more weird thing about this weird Portland tradition: While waiting for sundown, kids burn off steam by sliding down the brown-grass hillside on sleds made from sheets of cardboard. Even without the weird birds, an evening of grass sledding doesn’t sound too bad.

For more detail on this weird Portland event, and a video preview of the swifts diving into the chimney, check out our blog post on the Chapman Elementary swifts.

2. Add a plastic troll to the Portland Troll Bridge.

On a lonely forest road on the outskirts of town, you’ll find the Portland Troll Bridge. This isn’t a polished work of art, but rather a community tradition…passersby over the years have attached dozens of little plastic trolls to the underside of an old railroad trestle. Browse the many quirky trolls or add your own! For more on this weird Portland favorite, check out our Portland Troll Bridge blog post.

3. Eat at a weird Portland restaurant.

There are a lot of weird restaurants in Portland, so here I’ll share just a few examples: 

McMenamins Kennedy School: McMenamins Kennedy School is just one of many delightfully quirky McMenamins restaurants, bars, theaters, and hotels in Oregon and Washington. McMenamins turns old buildings–everything from abandoned schools to the old county poor farm–into elaborate destinations. 

McMenamins Kennedy School used to be a school, but now it’s a hotel, complete with a movie theater, restaurant, bar, and swimming pool. You don’t have to be a guest at the hotel to eat or catch a movie at the theater. Make sure to wander the halls, jam-packed with a mix of bizarre art and historical photographs. 

The Kennedy School is a great place to start, but Portland and the broader region are dotted with fabulously weird McMenamins establishments. The McMenamins brothers, Portlanders themselves, founded this weird & wonderful regional chain. Other favorites include the Bagdad Theater in SE Portland and McMenamins Historic Edgefield Manor in Troutdale.

4. Go to a weird Portland event.

Like eateries, there are too many weird Portland events to highlight them all. Here are a few to get you started: 

PDX Adult Soap Box Derby: Every August, spectators flood Mount Tabor Park in SE Portland, jostling to see contestants race down the extinct volcano in homemade soap box cars. There are honors for winning the race, but also for putting together the most fabulous cars and costumes (past favorites included a car that looked like a cup of ramen noodles, and another decked out as a giant sheep). Many contestants spray water over the crowd as they speed down the slopes. 

West Coast Giant Pumpkin Regatta: October brings the beloved West Coast Giant Pumpkin Regatta to the Portland suburb of Tualatin. A huge crowd turns out to watch dozens of costumed contestants race across a lake in dugout giant pumpkin “boats.” There’s nothing speedy about paddling around inside a giant pumpkin, but watching a bunch of adults trying to make this work is a great way to set aside reality for an afternoon and imagine you’re reliving James and the Giant Peach. 

Santa Clones: December brings the return of the Santa Clones to Portland. Artist Chris Willis hides dozens of plastic Santa figurines every year in an empty storefront. He shares clues on his Instagram for those who would like to join the hunt. Check out our video below for a look at a past year’s Santa clone hunt.

5. Play a piano outdoors in a park.

Every summer, nonprofit Piano.Push.Play ensures a fleet of most unusual pianos are deployed to Portland’s parks. Check out this fabulous tiger piano that appeared last year on top of Powell Butte, another of the Portland volcanoes. Stop by a park to play the piano or bring a picnic and listen to the music played by other passersby.

6. Watch a free (and mostly unrehearsed!) Shakespeare play in a park.

I can’t move on from the topic of parks without mentioning the Original Practice Shakespeare Festival, which brings free Shakespeare to Portland’s parks every summer. We happened to walk by one of these fabulously odd Shakespeare renditions in SE Portland’s Laurelhurst Park one summer afternoon, but check the website for the schedule so you can plan your shows. 

Just know before you go–you’ll never quite see Shakespeare performances like these. The Original Practice Shakespeare Festival prides itself on being true to the roots of Shakespeare performances–actors held and read from the scripts during the shows! You just never know what might happen.

7. Float down the Willamette River in a hot tub. 

We first encountered this weird Portland attraction while watching the annual Christmas Ships Parade. As we shivered on the banks of the Willamette River, watching the lighted boats go by, I noticed one of the boats was not moving along the parade route with the others. It was floating there, its occupants taking in the holiday lights as they lounged in a steaming hot tub. 

It turns out that you and up to five friends can rent a floating hot tub of your own from Portland Yacht Tubs for a river cruise that definitely makes the weird list.

8. Catch a performance by the Unipiper.

The Portland Unipiper is something of a living legend–who wouldn’t want to watch a unicycler pedal the streets while playing bagpipes that emit streams of fire? But you’ll have to be lucky to spot the Unipiper in action; as far as I can tell, there’s no schedule of events. We have yet to see the Unipiper himself, but we were delighted to spot another unicycling bagpipe player wheeling along in front of Mount Tabor Park one afternoon. Check out the photo below! 

9. Climb the city’s 4 volcanoes.

Luckily, none of the 4 volcanoes in Portland’s city limits are active, and they’re all quite small as volcanoes go. But still, Portland is probably one of the only cities where you can climb four volcanoes in an afternoon! Check out these four volcanoes-turned-city-parks: 

• Mount Tabor
• Powell Butte
• Kelly Butte
• Rocky Butte

10. Visit the Grotto, the weirdest Catholic church you’ll likely find.

You don’t have to be Catholic to appreciate the Grotto, a Catholic church in NE Portland whose sanctuary is carved right into an enormous cliffside, like a cave. The Grotto is perhaps best known for its over-the-top annual Christmas light display, but visit during daytime hours to take the huge elevator up to the top of the cliff. There you’ll find a clifftop mesa planted with extensive gardens.

For a virtual tour of this delightfully weird thing to do in Portland, check out our video below.

11. Take on the hunt for weird & wonderful “PDX Sidewalk Joy.”

Take to the neighborhood streets to see Portland’s weirdness really shine. The PDX Sidewalk Joy map allows you to navigate from one weird piece of neighborhood art to the next. At first glance, you may think Portland is filled with Little Free Libraries, but look closer–many of those tiny kiosks are not for books at all. You’ll find a dinosaur figurine exchange, sidewalk puzzle exchanges, a rubber duck exchange, a little hutch filled with poems etched onto pottery, and so much more. 

My favorite is a kiosk of free flower arrangements–every morning, the artist sets out vases of free flowers for passersby to take home. Just remember to return the vase so she can fill it for the next visitor! 

For a preview of these unusual sidewalk treasures, check out our video below.

12. Discover the unknown at the Zymoglyphic Museum.

Like the Portland Troll Bridge and PDX Sidewalk Joy, the Zymoglyphic Museum isn’t an official museum, but rather a reflection of the creativity of everyday Portlanders. Set up in a SE Portland garage, the Zymoglyphic museum looks like a museum about the Zymoglyphic region…except that the Zymoglyphic region doesn’t exist. It’s fanciful, creative, and just…weird.

13. Hike to the Witch’s Castle…AKA an abandoned park bathroom.

Portland is home to one of the largest urban forests in the US–the totally uncreatively named Forest Park. One of Forest Park’s most popular hikes has a name that’s as intriguing as “Forest Park” is dull…the Witch’s Castle. 

Walk along a moss-lined stream and you’ll indeed come upon an overgrown stone fortress. Just know that it definitely wasn’t a castle, nor was it inhabited by a witch. It was, in fact, a park bathroom that was abandoned dozens of years ago when a storm wrecked the plumbing. 

That doesn’t at all mean it isn’t a fabulous hike, but it is definitely weird.

For a virtual tour of the Witch’s Castle hike, check out our video below.

Other Adventures in the Pacific Northwest

Thanks for joining us for these 13 weird things to do in Portland! For more adventure ideas in the Pacific Northwest, check out our PNW Trip Planner. You can find adventures near you and filter by season and difficulty level. There are weird and wonderful things to explore any time of year. The trip planner links to blog posts to help you plan your next adventure.

Happy exploring!