Plan Your Weekend
The 8 Portland events worth planning your weekend around, chosen from everything on the PDX Events calendars. Also posted on Instagram.
Live Comedy
It's cuffing season! One of Portland's incredible live dating shows takes over the cozy stage at McMenamins Al's Den. Part matchmaking, part roast — contestants field questions while the crowd plays wingman. A little chaotic, a lot of fun, and a great way to meet friends and potential partners.
Al's Den · 6:30 PM
Street Fair
SE Belmont shuts down for its annual street party — local makers, food carts, live music, and beer gardens stretched along the strip. Wander, snack, and soak up peak late-summer Portland weirdness. It's free to roam all day.
SE Belmont St · 10 AM–5 PM
Oktoberfest
Steeplejack turns its NE Broadway brewery — a gorgeously converted old church — into an Oktoberfest hall for the day. House lagers, Bavarian bites, and steins all afternoon. Free to get in, family-friendly, and pours run till 8.
Steeplejack Brewing · 12–8 PM · Free
Centennial
The iconic Bridge of the Gods turns 100, and Cascade Locks throws a Gorge-side party to mark it — history, live music, food, and one of the most jaw-dropping backdrops in Oregon. Worth the scenic drive east for a day trip out of the city.
Port of Cascade Locks · 12–8 PM
Feel-Good
Guide Dogs for the Blind hosts a public graduation where puppy raisers hand off their dogs to the new handlers they'll change life for. It's exactly as heartwarming as it sounds — free, open to all, out in Boring.
Boring, OR · 1:30 PM · Free
Themed Brunch
Pull up in your convertible listening to "Just Dance" by Lady Gaga, please. The Social Spoon throws an all-Britney brunch — pop anthems, themed cocktails, and a menu to match. Grab the crew, dress the part, and make a Sunday of it.
The Social Spoon · 12–2 PM
Farm Festival
Tryon Life Community Farm celebrates apple season with fresh-pressed cider, live music, farm tours, and hands-on fun on its wooded SW Portland land. Ten bucks buys a mellow, kid-friendly afternoon in nature.
Tryon Life Farm · 1–4 PM · $10
Live Music
Portland's own a cappella pirates drop anchor at Canton Phoenix for a night of raucous sea shanties and original "piraty" parodies. Costumes encouraged, sing-alongs guaranteed. Cap the weekend with something delightfully, gloriously weird.
Canton Phoenix · 8:30 PM
Want more? See everything happening this weekend or the full Portland events calendar.