Everything costs money nowadays. Parking. Filtered water. Calling your mom. But it’s the basics—food, shelter, healthcare and the toilet paper to wipe your ass—that cost the most. So when it comes to enjoying the finer things in life, it makes sense that “fun” might feel out of reach in our late-stage-capitalist hellscape.
But maybe not. Here are a few ways to treat yourself to a good time without needing to Venmo-request your parents or ration your antidepressants.
INDOOR
Visit an Art Gallery
Check out First Thursdays at the Pearl District galleries or the Portland Art Museum, which offers free admission on certain nights. The Blue Sky Gallery is a great spot to spy photography, or venture across the river to the Alberta Arts District and stop into the Alberta Street Gallery to see work from 30 local artists.
Game Night, But Make It Chaotic
Write everyone’s name on slips of paper, tape them to foreheads and guess who’s who. Break out Monopoly if you’re in the mood to ruin a perfectly good evening—or Risk if you’re ready to lose friends and territories. Learn to play dominoes for points and let the winner claim a bizarre household prize (like all the condiments in the fridge). Play Mafia. Get messy. Get weird. Get loud.
Bar Comedy Shows
Lots of bars host free comedy nights. You don’t have to drink (though you do have to be 21+). Order a coffee, bring your discussion posts and let the laughs carry you through your due dates. If someone asks why you’re not drinking, try: “I’m sober and just here for the vibes—also, alcohol kills more people than all other drugs combined. Cheers!”
Dollar Tree Olympics
Hit up your local Dollar Tree with five bucks and a dream. Paint wine glasses. Buy squirt guns. Host a foam sword duel. Make it stupid. Make it yours.
OUTDOOR
Street Art Tour
Use the site Portland Wild to hunt down Portland’s iconic murals and street art. My personal favorite? A giant Ruth Bader Ginsburg with the words “La Lucha Sigue” (the fight continues), located at SW 11th & SW Yamhill St. Bring your camera, a friend, or just some headphones and a podcast.
DIY Scavenger Hunt
Portland has so many beautiful neighborhoods, all with an abundance of unique sights. Challenge yourself to find a pastel house, a vintage car or that weird tree shaped like a fork. Want more chaos? Ask your cleverest friend to hide your keys somewhere and leave clues—Escape Room meets real life.
Bird Watching
Download the Cornell Lab’s “Merlin Bird ID” app and start identifying those chirpy friends you usually ignore. Urban birding is surprisingly meditative—and free. My personal favorite is the starling, which I have spotted several times by Poet’s Beach. It’s like Pokemon Go, but with birds.
SEASONAL
Starlight Parade
Free. Wild. Loud. Sparkly. What’s not to love? It happens once a year, so plan ahead and bring snacks. Held annually during Rose Festival season, it takes over downtown with bedazzled floats, dance teams in LED costumes, unicyclists wearing wings and at least one dude in a full Darth Vader outfit throwing glow sticks. It’s like if Mardi Gras, a Pride march and your third-grade holiday pageant had a glitter-covered baby.
Saturday Market at the Northwest Waterfront
During the warmer months, the waterfront market is home to beautiful art, talented craftsmen and handmade fashion. Take the streetcar down or enjoy the short walk over. Window shop. Make awkward eye contact with glass-blowing guys. You don’t have to buy a dang thing. If you’re lucky, there will be a musician with a trumpet or saxophone playing jazz–recline by the water and enjoy a soulful start to your day.
Big fun doesn’t have to mean big money. Most of the time, the best adventures come from a little creativity and a refusal to let capitalism steal your joy.
