A Fun-filled Guide to Spending Labor Day 2022 Weekend in Portland


And just like that, summer is almost over. But you can still go on one last summer getaway this Labor Day 2022! You don’t have to look far; Portland has a lineup of exciting events and incredible exhibits, whether you are spending it alone or with your loved ones. 

Savor the last of summer with good food, booze, indie music, and local arts. Portland awaits with a ton of Labor Day weekend events, from the exhilarating Grand Prix to whimsical art exhibits. End the summer with a bang and visit this quirky city. Here are some fun things to do on Labor Day weekend in Portland:


Grand Prix of Portland

When: September 2-4, 2022

Where: Portland International Raceway, 1940 N Victory Blvd, Portland, OR, 97217, USA

Satisfy your need for speed and catch an open-wheel race at the annual autumn Grand Prix of Portland event. Feel your adrenaline rush as you watch your favorite racers go head-to-head at the open-wheel racing event.


One of the most anticipated Labor Day weekend events in Portland, this race is unlike any other because it isn’t run on a simple oval. Instead, the race features 12 turns and several exciting passing opportunities. Backed by one of the most exciting racing schedules in the country, this year’s event will be held on September 1-3. If you’re a racing fan, this is an event not to miss! Visit their website for the full line of events and schedule. 


Art In The Pearl Fine Arts & Crafts Festival

When: September 3-5, 10am-6pm

Where: Northwest Park blocks of Portland, Oregon, between W Davis and NW Flanders at NW 8th Avenue

Get your creative juices flowing at the Art In The Pearl—Portland’s exclusively artist-run outdoor fine arts and craft festival. Celebrating its 26th anniversary this Labor Day 2022, the unique event offers a wide variety of original works, including paintings, sculpture, ceramics, photography, fine jewelry, and more. Stroll among rows of freestanding exhibits under the canopy of trees in the beautiful North Park Blocks. It’s a fun art shopping experience for veteran art collectors, newcomers, and families. Plus, you get an opportunity to meet local artists. Learn more about this free event at their website


Lose Yr Mind Indie Music Festival 

When: September 2-3, 2022

Where: 4 venues – Vitalidad, Bunk Bar, or Lollipop Shoppe (FKA Dig A Pony) + The Getdown

This is one of the exciting things to do in Portland on Labor Day weekend. Lose Yr Mind Fest is celebrating its eighth most significant year yet. This massive event features over 30 bands over two days in 4 unique venues. It is easily accessible by bike, foot, or SE Portland. Time to party, get sweaty with friends or strangers. Swig that bottle of beer as you lose your mind to indie music, whether in Vitalidad, Bunk Bar, or Lollipop Shoppe (FKA Dig A Pony) + The Getdown. It’s all about the music, so grab a wristband and come enjoy great bands, food trucks, and tasty beverages at the festival. One wristband gets you access to all of the venues. For more information and to buy your tickets, visit loseyrmind.com


Happy Hour Crafts and Pints – Painting Class by Classpop!™

When: Saturday, September 3, 2pm

Where: DIY Bar, 3522 N Vancouver Ave, Portland, OR 97227

Happy Hour Crafts and Pints is for you if you’d rather spend your Labor Day weekend learning a new skill while sipping on your favorite drinks. Learn and practice unique painting techniques in a fun, social setting. You’ll enjoy creating unique artwork as a beginner or advanced painter as you explore captivating mediums, brushstroke techniques, and more. ClassPop is also a great way to catch up with friends. It offers creative classes such as dance and pottery in relaxed settings guided by world-class instructors. Visit their website to register.



Curious Comedy Showdown

When: September 3-4, 2022 

Where Curious Comedy Theater, 5225 NE Martin Luther King Jr Blvd, Portland, OR 97211

Want to blow off some steam and get a good laugh? Check out Curious Comedy Showdown. Dubbed as the “Hunger Games of Comedy,” the show pits Portland’s best comedians against one another in competitive improv comedy cage matches that will leave you laughing until you cry.

With only razor-sharp wit and audience suggestions, the comedians must create fast-paced and hilarious scenes on the spot to win audience votes – round after round. Finally, you decide which player is left standing.

Watch the flagship improv show in person at the main stage venue in Northeast Portland, or watch the hilarious Livestream from your hotel while drinking a glass of wine. Secure your tickets HERE.



Portland Parks and Recreation’s Summer Free for All program 

When: September 3, 202, 7:30pm

Where: Woodstock Park SE 47th Ave & Steele St Portland, OR 97206

You don’t have to spend a dime to have a good time. If you’re looking for free things to do in Portland this summer, pack up your picnic blanket and sunblock and head to Portland Park. The park offers fun anytime, but the Summer Free for All program ups its game, offering free events all summer including free movie screenings, concerts and swimming pool access. On September 3, join in the fun and watch the movie, Soul. Bring in your family and friends and enjoy the film under the Portland stars.



Turn your OOO on and head to Portland this Labor Day 2022. Enjoy a relaxing staycation in Ponderosa Inn and get away from the hustle and bustle of the city on the weekend. Nothing says Labor Day like relaxing in our jacuzzi while taking in the scenic view of Portland Parks. We are located just 30 minutes away from Portland – in a charming suburb that offers peace and tranquility. Reserve your room now.

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