Day · Live Music
Dan Hubbard
Free live music at Covert Café — Dan Hubbard brings his style to one of Portland's cozy neighborhood spots. No cover, 21+.
Covert Café · 4 PM · Free · 21+
Events of the Week
Best Things to Do in Portland: Jul 20–26, 2026
14 hand-picked events for the week — a daytime and an evening pick for each day, chosen from everything on the PDX Events calendars. Also posted on Instagram.
Monday, July 20
Night · Spoken Word
Poet vs. Poet Slam
Two poets face off, and the audience decides. Portland's competitive spoken word scene at its most raw and electric.
Barrel Room · 7 PM
Tuesday, July 21
Day · Craft
Pride Piñata Making
Bilingual, all-ages craft workshop at Central Library — make your own piñata and celebrate Pride. All materials provided, no registration required.
Central Library · 1 PM · Free
Night · Social
Chuesday
Wonderlove's weekly Tuesday gathering — a welcoming spot for an early-evening drink and dancing. Free entry!
Wonderlove · 5 PM · Free
Wednesday, July 22
Day · Swimming
Free Swim at Grant Pool
Cool off at one of Portland's beloved outdoor pools. Portland Parks runs free open-play swim sessions all summer — no registration needed, no cost.
Grant Pool, NE 33rd · 1 PM · Free
Night · Live Music
Duckworth Wednesdays
The vibes are immaculate at Duckworth Wednesdays — bring snacks and some drinks, chill on the dock or in the water, and soak in the sunset while listening to free music. The dock gets busy so be prepared to get there early or pack in close.
Lloyd Esplanade · 5:30 PM · Free
Thursday, July 23
Day · Market
SW Farmers Market
Every Thursday in South Waterfront — local farmers and artisans with fresh produce, specialty goods, and prepared food. Free to browse all afternoon.
South Waterfront · 12 PM · Free
Night · Dance
Art in the Dark
AWOL Dance Collective performs aerial dance among the trees in Mary S Young Park at dusk — suspended performance as natural light fades. Tickets are a little $$, but this is a unique experience.
Mary S Young Park, West Linn · 9 PM · $45
Friday, July 24
Day · Tech
Teardown 2026
Crowd Supply's annual open hardware conference at the Jupiter Hotel — talks, demos, and community for engineers, makers, and electronics enthusiasts. All-day celebration of building things. Pre-registration required.
Jupiter Hotel · 9:30 AM
Night · Opera
Mariachi Opera in the Park
A free outdoor performance of "Cruzar la Cara de la Luna" — a Grammy-winning mariachi opera blending classical storytelling with the soul of traditional Mexican music.
6:30 PM · Free
Saturday, July 25
Day · Street Fair
Community Blocks Street Fair
SE 42nd Avenue closes for a full day of live music, food trucks, comedy, a beer garden, and an art walk. Family-friendly, all-ages, and completely free.
SE 42nd (Francis–Holgate) · 10 AM · Free
Night · Dance Party
90s & 2000s GLOW Night
Break out the neon — Crystal Ballroom's GLOW Night brings back the best of the 90s and early 2000s for a blacklight dance party on Portland's most iconic dance floor. This will be packed with millennials ready to boogie. If you like to dance, check this one out.
Crystal Ballroom · 8 PM
Sunday, July 26
Day · Street Fair
Montavilla Street Fair
The Montavilla neighborhood's beloved annual street fair returns to SE Stark Street. Local vendors, food, live music, and community energy — all free, all day.
SE Stark & 76th · 10 AM · Free
Night · Fun & Games
Rubber Duck Races
Adopt a numbered rubber duck, cheer it on to the finish line, and enjoy the beautiful silliness of competitive waterfowl racing. This is the Portland whimsy you're looking for.
Starday Tavern · 4 PM · Free
Want more? See everything happening this weekend or the full Portland events calendar.