17 Things to Do in Bend OR This Week · June 25–28, 2026

Arts & Culture

Once Upon a Mattress

Ponderosa Players perform this uproarious musical comedy based on Hans Christian Andersen's 'The Princess and the Pea' at Ponderosa Playhouse.

Thursday, June 25, 2026 7:00 PM · Ponderosa Playhouse, 211 NE Revere Avenue, Bend

Oregon Origins Project VIII: Echoes of Eruption – Stories of the Northern Paiute

Wilson Wewa shares Northern Paiute oral traditions in the opening night of this multimedia exploration of Newberry Volcano, Oregon's largest in the Cascade Range.

Thursday, June 25, 2026 7:30 PM · Tower Theatre, Bend

Free Events

Alpenglow Nights Free Concert

Free live music in SE Bend's Alpenglow Community Park every Thursday evening this summer — bring a picnic and enjoy food and drinks on the lawn.

Thursday, June 25, 2026 5:00 PM · Alpenglow Community Park, SE 15th Street, Bend

2026 Invent Oregon Finals

Watch student innovators compete in the Invent Oregon Finals at OSU-Cascades — a free event celebrating entrepreneurship and invention.

Friday, June 26, 2026 10:00 AM · Oregon State University-Cascades, Bend

Friday Community Walk & Breathwork at Farewell Bend

Join Bend Breathwork for a free community outdoor walk and breathwork session at Farewell Bend Park.

Friday, June 26, 2026 5:00 PM · Farewell Bend Park, Bend

FREE Pure Barre in the Park

A free outdoor Pure Barre fitness class in Riverbend Park — bring a mat and get your summer sweat on alongside the river.

Sunday, June 28, 2026 9:00 AM · Riverbend Park, Bend

Date Night

Live at the Vineyard: Mango Stew

Mango Stew brings Palm Tree Rock 'N Roll island vibes to Faith Hope and Charity Vineyards for an evening of tropical tunes and vineyard atmosphere.

Thursday, June 25, 2026 5:00 PM · Faith Hope and Charity Vineyards, Terrebonne

Parasol Rooftop Bar Season

Bend's secret seasonal rooftop bar, Parasol — operated by Zydeco Kitchen & Cocktails — is open this summer on a prominent downtown building for drinks above the city.

Saturday, June 27, 2026 · Downtown Bend (Zydeco building)

Music & Nightlife

Bend Bachelorette Comedy Show at Coyote

Bits N Skits Productions hosts a comedy-forward bachelorette show with live music from Atillion and matchmaking fun at Coyote bar.

Thursday, June 25, 2026 6:00 PM · Coyote, NW Harriman Street, Bend

AROMA Thursdays Latin Dancing

Weekly Latin social dance night hosted by Bend Latin Dancing Meetup — open to all levels.

Thursday, June 25, 2026 7:30 PM · Bend

Parker McCollum

Country star Parker McCollum headlines Hayden Homes Amphitheater with guests Vincent Mason and Aubrie Sellers.

Friday, June 26, 2026 5:00 PM · Hayden Homes Amphitheater, Bend

The Big Drunk Spelling Bee

A live comedy game show where eight contestants battle impossible words and a table full of beer — four comedians host the chaos at Silver Moon Brewing.

Friday, June 26, 2026 7:00 PM · Silver Moon Brewing, NW Greenwood Avenue, Bend

Festivals & Special Events

Big Ponderoo

The fourth annual Big Ponderoo returns to Sisters for two days of Americana and bluegrass featuring The California Honeydrops, Steep Canyon Rangers, Fruition, and more under towering ponderosa pines.

Friday, June 26, 2026 5:00 PM · Village Green Park, Sisters, OR

Deschutes 38th Anniversary Drag Brunch

Sequins, sips, and Saturday shenanigans — Deschutes Brewery celebrates 38 years with a full drag brunch at the Bend Public House.

Saturday, June 27, 2026 10:00 AM · Deschutes Brewery – Bend Public House, NW Bond Street, Bend

Sports

Cascade Lakes Relay

A 216-mile overnight team relay race through mountain landscapes and the Cascade Lakes Highway, finishing near the Deschutes River at Bend's Old Mill District.

Friday, June 26, 2026 · Old Mill District, Bend (finish)

Food & Drink

Oregon Margarita Festival

The inaugural Oregon Margarita Festival hosted by the International Margarita Organization comes to The Bite in Tumalo for a full afternoon of margarita competition and fun.

Saturday, June 27, 2026 12:00 PM · The Bite, Tumalo

Outdoors & Active

Crux Fermentation Project 5K Beer Run

Oregon Brewery Running Series partners with Crux Fermentation Project for a fun 5K through Bend, finishing with a craft beer and mountain views at Crux's renovated outdoor space.

Saturday, June 27, 2026 · Crux Fermentation Project, Bend