16 Things to Do in Bend OR This Week · May 21–24, 2026

Music & Nightlife

Brandi Carlile Night 2

Second night of Brandi Carlile's two-night stand at the Hayden Homes Amphitheater with special guest Kristin Key.

Thursday, May 21, 2026 5:00 PM · Hayden Homes Amphitheater, Bend

Long Gone Wilder – Live Music @ Portello Lounge

Local act Long Gone Wilder plays a two-hour live set at the intimate Portello Lounge in NW Bend.

Friday, May 22, 2026 7:00 PM · Portello Lounge, 2754 NW Crossing Dr., Bend

Unofficial Claypool Gold Afterparty – Shafty at The Domino Room

Keep the night going with Shafty's tribute set at The Domino Room as the unofficial afterparty for Claypool Gold.

Friday, May 22, 2026 9:30 PM · The Domino Room, Bend

Katacombs – Bend's Premier Goth Night

Post-punk, darkwave, and industrial DJ sets fill The Domino Room for Bend's premier all-ages goth night — $15 cover, 21+ for alcohol.

Saturday, May 23, 2026 7:00 PM · The Domino Room, Bend

I'm With Her at Tower Theatre

Folk supergroup I'm With Her (Sara Watkins, Sarah Jarosz, Aoife O'Donovan) performs in the intimate Tower Theatre setting.

Sunday, May 31, 2026 7:30 PM · Tower Theatre, Bend

Free Events

Alpenglow Nights

Season opener of the beloved summer series bringing live music and community vibes to Alpenglow Community Park every Thursday evening.

Thursday, May 21, 2026 5:00 PM · Alpenglow Community Park, Bend

Bend Run Club at Crux Fermentation Project

Weekly Tuesday run club meetup this month based at Crux Fermentation Project — show up at 6pm, run, then enjoy a beer with the community.

Tuesday, May 26, 2026 6:00 PM · Crux Fermentation Project, Bend

Bend Farmers Market – Wednesday Market

The downtown Bend Farmers Market runs every Wednesday on Brooks Alley — free to browse with local produce, vendors, and food.

Wednesday, May 27, 2026 11:00 AM · Brooks Alley, Downtown Bend

Outdoors & Active

GetUpandGroove Morning Dance at Jackstraw

Coffee, music, and morning dance vibes at the grand opening of Sisters Coffee at Jackstraw — dress festive and bring friends, kids welcome.

Friday, May 22, 2026 8:00 AM · Jackstraw Bend, 310 SW Industrial Way Suite 110, Bend

Smith Rock Classic

Trail runners take on 50-mile, 50K, and 10-mile courses through Smith Rock State Park and the Crooked River Grasslands, finishing with beer and prizes.

Saturday, May 30, 2026 · Smith Rock State Park

Food & Drink

Maison Kokoro French-Asian Patisserie Pop-Up

Chef Maya Howell's debut French-Asian patisserie pop-up returns to Pika Pika serving laminated pastries like croissants and danishes infused with ube and yuzu.

Saturday, May 23, 2026 11:00 AM · Pika Pika, Downtown Bend

Bend Brews & Beyond

Oregon's largest brewfest returns to Drake Park with 50+ breweries, 100+ beers, live music, a DJ, the Hempgarten, and the Drinking Pants Pageant.

Saturday, May 23, 2026 12:00 PM · Drake Park, Bend

Fiber & Flame Society May 2026 Gathering

Monthly gathering of the Fiber & Flame Society — a creative community meetup combining crafts and conversation.

Thursday, May 28, 2026 4:00 PM · Bend

Festivals & Special Events

Bend Summer Fest

Downtown Bend's signature summer kickoff returns May 29–31 with live music, fire performers, circus arts, local food and drink, and nonstop street energy.

Friday, May 29, 2026 · Downtown Bend

Build Something That Matters Hackathon

A tech-focused hackathon for builders who want to create something meaningful — hosted by What the Tech, Bend?

Friday, May 29, 2026 2:00 PM · Bend

Arts & Culture

Kaleidoscope – Bend Dance Project

Bend Dance Project presents Kaleidoscope, a general-admission dance showcase at the Tower Theatre with adult and student pricing.

Saturday, May 30, 2026 7:00 PM · Tower Theatre, Bend