Day · Food Class
Oysters 101
Flying Fish's crash course in all things bivalve — how to shuck, slurp, and tell your Kumamotos from your Shigokus, with plenty to taste along the way. A briny, hands-on way to start the week.
Flying Fish · 6 PM
Events of the Week
Best Things to Do in Portland: Sep 14–20, 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 14
Night · Watch Party
90 Day Fiancé Tell-All
Jackie's throws a rowdy 21+ watch party for the 90 Day Fiancé Tell-All — the messiest night on reality TV, best experienced with a room full of fellow obsessives. Come for the drama, stay for the group gasps.
Jackie's (SE Sandy) · 6:30 PM · 21+
Tuesday, September 15
Day · Cultural Festival
El Grito Portland
Portland's biggest ¡Grito! rings in Mexican Independence and Hispanic Heritage Month at the Moda Center — free, all day, and packed with music, dance, food, and family activities. A joyful kickoff to the celebration.
Moda Center · 11 AM–10 PM · Free
Night · Free
Swift Watch
September's magic hour: thousands of Vaux's swifts spiral into the chimney at Holy Trinity Church (or other locations around the metro area) at dusk before roosting for the night. Bring a blanket, watch these tiny majestic birds turn the sky into a dancing vortex. Please be respectful of the birds and the neighbors.
Holy Trinity Greek Orthodox · 7:30 PM · Free
Wednesday, September 16
Day · Food Week
PDX Fried Chicken Week
A week-long, citywide excuse to eat fried chicken — participating spots serve $10 specials Sept 14–20, from classic buckets to Nashville-hot and Korean-style. Pick a new place each day.
Various restaurants · All week · $10
Night · Only in PDX
Li'l Coffee Shop of Horrors
Geek Week takes over Sinister Coffee & Creamery with a playful Little Shop of Horrors–themed night — spooky sweets, themed drinks, and campy fun. A weird, sugary midweek treat.
Sinister Coffee & Creamery · 7:30 PM
Thursday, September 17
Day · Free Concert
DJ George the Mixologist
Director Park's downtown plaza gets a free midday soundtrack from DJ George the Mixologist. Grab lunch nearby, post up in the sun, and let the beats carry the afternoon.
Director Park · 11 AM · Free
Night · WNBA
Fire vs. Phoenix Mercury
Portland's brand-new WNBA team, the Fire, hosts the Phoenix Mercury at the Moda Center. Catch pro women's basketball in its inaugural PDX season — the crowd energy alone is worth the ticket.
Moda Center · 7 PM
Friday, September 18
Day · Oktoberfest
7th Annual Elktoberfest
The Vancouver Elks throw a free, family-friendly Oktoberfest across the river — brats, brews, live music, and games. An easy, low-key way to kick off Oktoberfest season.
Vancouver Elks · 4 PM · Free
Night · Live Music
Gregory Alan Isakov + Oregon Symphony
The beloved Colorado folk songwriter plays with the full Oregon Symphony behind him at the Schnitzer — lush, cinematic, and made for a big hall. One of the prettiest shows of the season.
Arlene Schnitzer · 7:30 PM
Saturday, September 19
Day · Street Fair
Belmont Street Fair
SE Belmont shuts down for one of Portland's weirdest, most beloved street fairs — local vendors, live music, art, and peak people-watching. Free, all day, unmistakably Portland.
SE Belmont · 10 AM–5 PM · Free
Night · Oktoberfest
Oktoberfest at Steeplejack
Steeplejack Brewing throws a free Oktoberfest at its NE Broadway taproom — house brews, German eats, and a festive fall crowd well into the evening. Prost!
Steeplejack (NE Broadway) · 12–8 PM · Free
Sunday, September 20
Day · Harvest Festival
Apple Festival
Tryon Life Community Farm celebrates the harvest with fresh-pressed cider, live music, farm tours, and hands-on fall fun tucked into the woods off Boones Ferry. A cozy, family-friendly Sunday.
Tryon Life Community Farm · 1 PM · $10
Night · Live Music
The Front Bottoms
The Jersey emo-folk favorites bring their "11 Years of Back On Top" tour to Revolution Hall — singalong anthems and rowdy, heart-on-sleeve energy. A loud, cathartic way to close the week.
Revolution Hall · 7 PM
Want more? See everything happening this weekend or the full Portland events calendar.