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A Bigfoot figurine stands among fallen leaves in a Pacific Northwest forest.

08 December . 2023

6 weird & wonderful winter outings near Portland, Oregon

While Oregon winters are famously known for gray skies and dreary days, Portland residents refuse to let the weather stop them from having fun. As locals will tell you, it’s actually the perfect time to explore some of the more eccentric attractions in the City of Roses. 

You may have heard the slogan “Keep Portland Weird.” As the city’s unofficial motto, the phrase refers to its quirky nature and tendency to attract homebuyers with a unique outlook on life. So, if you’re looking for something new to do this winter, read on for some of our favorite “weird” activities to help you make your days more wondrous.

Close-up of a butterfly with black and white wings against a background of green leaves.

Cool & unusual museums

From weird science to cryptozoology, Portland has multiple museums dedicated to the unusual and bizarre. For a day of wackiness, we recommend starting at the Freakybuttrue Peculiarium in the Northwest District, where you can have your insides examined by extraterrestrial beings, munch on edible insects, or snap a photo with Krampus, the anti-Santa, as he sits atop his throne. 

Next, head to Sellwood to visit the Portland Puppet Museum. It’s the only permanent museum dedicated to puppetry on the West Coast, with a lovingly curated collection and a passionate staff that practically guarantees you’ll learn something new. From there, it’s a quick walk or drive over to the Portland Insectarium, the city’s first museum dedicated entirely to insects and arachnids. This kid-friendly experience started out as a pop-up, but quickly became so popular that it got its own permanent space!

A gray whale breaches the surface of dark ocean waters.

Whale watching on the Oregon coast

Every year, more than 20,000 gray whales pass by the Oregon coast as they journey south toward the warm waters of Mexico. Starting in mid-December and continuing through January, migrating whales can be seen in numerous locations along the coastline—but one of the best places to catch this epic event is Depoe Bay, known as the “whale watching capital of Oregon,” which is located about 90 miles from Reed’s Crossing.

To celebrate the migration, Oregon Parks and Recreation hosts biannual Whale Watching Weeks, with volunteers stationed at multiple sites along the coast during peak migration times. Don your warmest jacket, pour a mug of your favorite steaming-hot beverage, grab your binoculars, and head out to the coast for a whale of a time!

The creepy Shanghai Tunnels run beneath the city of Portland, Oregon.

Go underground in the Shanghai Tunnels

The rain can’t get to you under the city! In the early 1900s, Portland was considered one of the most dangerous ports in the world. The Portland Underground, more commonly referred to as the Shanghai Tunnels, was a series of bar and hotel basements linked to each other, and to the Willamette River docks, by an elaborate system of tunnels. 

While the tunnels were mostly used for above-board practices, like keeping supplies dry, they were also home to more dangerous deeds. Today, join Cascade Geographic Society and resident ghost, Nina, for tours that highlight a former opium den and more mysterious spaces—now with an additional 4,400+ square feet of underground space never before seen by the public!

Selective focus photo of a latte in a green mug on a dark wood table.

Watch your latte run away at Rimsky-Korsakoffee House

Housed in a Victorian home in Southeast Portland, the Rimsky-Korsakoffee House boasts a kooky atmosphere alongside incredible desserts, and is said to be haunted by its former tenants, writers who witnessed the Russian revolution.

Many of the tables in this local fave actually move—from shrinking vertically to rotating slowly (hence the runaway latte.) And if you ask for water, you may get squirted by a water gun rather than receiving it in a glass. It’s a great spot to take out-of-towners for a taste of the “weird” side of Portland!

A holiday light display features large balls wrapped with lights stacked to form a pyramid.

Light it up at the Portland International Raceway 

You may not be able to zip around in a racecar, but you can still tell your friends that you spent your night cruising the track during Winter Wonderland at the Portland International Raceway (PIR). 

Dubbed the “Largest Holiday Light Show West of the Mississippi,” this spectacular drive-through experience is open every evening through January 1. Bundle up, hop in the car, and head on down to enjoy an amazing light-filled experience, where visitors drive around the racetrack to view over 250 set pieces and animated scenes. Pro tip: book your ticket for weeknights or head over to PIR within the first hour of opening to avoid long wait times!

Selective focus shot of a group of roller derby skaters as they fly by the camera.

Joyful jamming with the Rose City Rollers

If you’re looking for an action-packed way to get out of the rain and a classic five-star Portland experience, head out to The Hangar at Oaks Amusement Park to catch the city’s famous four-time roller derby world champions, the Rose City Rollers!

With a home season that starts in January, this all-female league attracts hundreds of rabid fans. If you’re new to roller derby, look for someone wearing an “Ask Me About Derby” shirt to get all your questions answered; reviews on Google rave about the “super friendly atmosphere” and “incredible athleticism” displayed as the teams battle it out to the end. Matches tend to sell out quickly, so be sure to check the schedule before you get ready to rumble! 

Curious about life in Portland, Oregon? See the hottest up & coming neighborhoods or check out 7 things you might not know about our beautiful state.