It’ll be a crisp fall welcome to October this weekend, and we’re suggesting you head out to enjoy events from the Portland Fall Fest to the Endless Wonders Book Fest and from the 73rd Annual Portland Greek Festival to the Portland Trail Blazers Fan Fest. For more ideas, check out our top picks of the week.
FRIDAY
LIVE MUSIC
Dairy Fest 2026: Milc & Friends
Kick off your weekend at the third annual Dairy Fest, an all-local lineup of hip-hop legends and rising rap stars curated by Portland artist Milc. The MC, who grew up rapping in Northeast Portland playgrounds, often makes dairy references, like in his newest song “Keno,” when he calls out the character Cheddar Bob from Eminem’s 2002 film 8 Mile. The night is hosted by Hasaan Thomas, the star of the dark comedy web series—and soon-to-be movie—Hasaan Hates Portland, while local producer Spinitch, who worked with Milc and Portland rapper Wynne on the atmospheric track “Mr. and Mrs. Smith,” holds down the decks with an all-vinyl hip-hop DJ set. Don’t miss melodic bars and trap beats from 3Way Heff, smooth verses from Jesse Desean, and street stories from rapper T.$poon. SHANNON LUBETICH
(Polaris Hall, Humboldt, $19.27)
