16 Things to Do in Bend OR This Week · June 11–14, 2026

Date Night

Live at the Vineyard: Heller Highwater Trio

An evening of live music at Faith Hope and Charity Vineyards — sip local wine while the Heller Highwater Trio performs in a scenic vineyard setting.

Thursday, June 11, 2026 5:00 PM · Faith Hope and Charity Vineyards, 70450 NW Lower Valley Dr, Bend

Amaterra Bend June Supper Session

An intimate prix fixe dinner experience at Amaterra Bend — a beautifully curated multi-course meal perfect for a special evening out.

Saturday, June 13, 2026 · Amaterra Bend, Downtown Bend

Joanna Lee @ Portello Lounge

Local artist Joanna Lee performs a live set at the intimate Portello Lounge in Northwest Crossing.

Saturday, June 13, 2026 6:30 PM · Portello Lounge, 2754 NW Crossing Dr., Bend

Trivia Night at Beach Hut Deli

Weekly Tuesday trivia night at Beach Hut Deli with Tip of the Tongue Trivia — test your knowledge for a chance at prizes.

Tuesday, June 16, 2026 6:00 PM · Beach Hut Deli, Downtown Bend

Music & Nightlife

Juniper Preserve Live Music: Brandon Campbell Trio

Free live music from the Brandon Campbell Trio at Coyote Lounge at Juniper Preserve, with drinks and tapas available for purchase.

Thursday, June 11, 2026 4:00 PM · Juniper Preserve, Pronghorn Club Drive 65600, Bend

Metric

Canadian indie rock band Metric performs at the Hayden Homes Amphitheater in an outdoor summer concert.

Wednesday, June 24, 2026 · Hayden Homes Amphitheater, 344 SW Selvin Hixon Drive, Bend

Outdoors & Active

Heroes on the Run — Dog-Friendly 5K, 10K & Kids Mini Run

A dog-friendly community run with 5K, 10K, and kids mini run options, starting at the Old Mill District.

Sunday, June 14, 2026 8:00 AM · Old Mill District, 450 SW Powerhouse Dr., Bend

Bend Run Club at 10 Barrel Westside

Bend Run Club meets every Tuesday at 10 Barrel Brewing Westside for a group run followed by post-run beers — all paces welcome.

Tuesday, June 16, 2026 6:00 PM · 10 Barrel Brewing Westside, Bend

Summer Solstice Women's Circle: Breathwork, Movement & Connection

A special Summer Solstice gathering featuring breathwork, movement, and community connection hosted by Bend Breathwork.

Thursday, June 18, 2026 6:00 PM · Bend

Family-Friendly

Dragonfly Farm and Arts Summer Camp Preview Visit

An open preview visit to Dragonfly Farm and Arts so families can explore summer camp offerings for kids in a farm and creative arts setting.

Sunday, June 14, 2026 1:00 PM · Ann Boyd, 18270 Rock Springs Rd, Bend

Arts & Culture

Rosie the Riveter – World Premiere Musical

The world premiere of 'Rosie the Riveter, A New Musical' presented by Thoroughly Modern Productions at the Tower Theatre.

Thursday, June 18, 2026 7:30 PM · Tower Theatre, 835 NW Wall Street, Bend

The Crazy Happy Silly Funny Nerdy Show

A comedy-focused variety show at Silver Moon Brewing bringing together multiple comedic styles and performers for a fun Tuesday night out.

Tuesday, June 23, 2026 7:30 PM · Silver Moon Brewing, Bend

Free Events

First Friday Art Walk – Old Mill District

Monthly First Friday Art Walk returns to the Old Mill District with featured artists, wine, and community — second floor above Sisters Coffee.

Friday, June 12, 2026 3:00 PM · Old Mill District, Bend

Community Song Circle in Bend

An uplifting community gathering centered around group singing, rhythm, and music-based wellness hosted by Rhythms of Wellness.

Saturday, June 20, 2026 10:00 AM · Bend

Old Mill District 25th Anniversary Dance Party

A free all-out dance party inside the Hayden Homes Amphitheater celebrating the 25th anniversary of the Old Mill District, featuring genre-blending mashups and remixes.

Saturday, June 20, 2026 6:00 PM · Hayden Homes Amphitheater, Old Mill District, Bend

Festivals & Special Events

Reggae Rise Up Oregon

Reggae Rise Up Oregon returns for its second year, a multi-day reggae music festival featuring live bands and the spirit of the islands in Bend.

Friday, June 12, 2026 8:00 PM · The Domino Room, Bend