Day · Cocktail Week
Negroni Week
Bars across Portland pour riffs on the classic Campari-gin-vermouth trio all week, often with proceeds going to charity. A citywide excuse to bar-hop and find the negroni variation you didn't know you needed.
Events of the Week
Best Things to Do in Portland: Sep 21–27, 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, September 21
Night · Live Music
Citizen
The Toledo-bred post-hardcore favorites bring their heavy-hearted anthems to the Wonder Ballroom. Expect big singalongs and to FEEL something.
Wonder Ballroom · 6 PM
Tuesday, September 22
Day · Immersive Art
Lookout Landscape
A new immersive forest-art exhibition at the World Forestry Center turns Oregon's woods into a walk-through of light, sound, and scale. Quiet, dreamy, and a lovely midweek reset.
World Forestry Center · 10 AM
Night · WNBA Basketball
Fire vs. Valkyries
Portland's brand-new WNBA team, the Fire, host Golden State's Valkyries at the Moda Center in their inaugural season. Get in on the ground floor of pro women's hoops in PDX.
Moda Center · 7 PM
Wednesday, September 23
Day · Community
Q+ & Ally Pro Meetup
A morning mixer for LGBTQ+ and ally professionals at Social Good Place — coffee, connections, and a warm, low-key start to the workday. New faces always welcome.
Social Good Place · 9 AM
Night · Free
Open D&D Night
Covert Cafe hosts a free, drop-in Dungeons & Dragons night — roll up with a character or just watch the chaos unfold. 21+, and no experience required.
Covert Cafe · 7–10 PM · Free · 21+
Thursday, September 24
Day · Festival
Radical Mycology Convergence
A multi-day gathering for the fungi-curious at Brown Bottle Farm — talks, workshops, and forays into all things mushroom. Passes slide from a single day to the full convergence.
Brown Bottle Farm · 12 PM · $12+
Night · After-Hours
Pittock Mansion Happy Hour
The historic mansion opens after hours for terrace views over the whole city and a cash bar from a rotating local winery - This time Dobbes Family Winery in Dundee. Golden-hour Portland at its absolute prettiest.
Pittock Mansion · 5:30 PM
Friday, September 25
Day · Oktoberfest
Stammtisch Oktoberfest
NE 28th's beloved German beer hall throws its annual Oktoberfest, with steins, brats, and Bavarian cheer spilling onto the patio all weekend long. Prost!
Stammtisch · NE 28th · All weekend
Night · Cultural
O-Tsukimi Moon Viewing
The Portland Japanese Garden celebrates the harvest moon with music, tea, and lantern-lit strolls through the grounds after dark. Serene, seasonal, and quintessentially fall.
Portland Japanese Garden · Evening
Saturday, September 26
Day · Fall Festival
Spirit of Halloweentown
The riverside town of St. Helens becomes the real Halloweentown — pumpkin lighting, movie sets, vendors, and spooky-season magic all day. A must for anyone who lives for October. This is opening day!
St. Helens · 11 AM · $20–50
Night · Pro Soccer
Thorns vs. Houston Dash
The Thorns take the pitch under the lights at Providence Park in front of one of the loudest, most electric crowds in women's soccer. Wear red and bring your voice.
Providence Park · 5:45 PM
Sunday, September 27
Day · Free Festival
El Festival de Mariachi
A free afternoon of mariachi, ballet folklórico, and family fun at the Hillsboro Ballpark celebrating Mexican music and heritage. Bring the whole crew and a folding chair.
Hillsboro Ballpark · 12 PM · Free
Night · Free
Cats of Sunnyside Cat Walk
The Cats of Sunnyside crew leads a leashed-cat (and cat-curious) stroll down SE Division — yes, really. Portland's most wholesomely weird way to close out the week.
SE Division · 4–6 PM · Free
Want more? See everything happening this weekend or the full Portland events calendar.