Concierge

7 Things to Do in Bend OR This Week · June 18–21, 2026

Top Picks This Week

★ Cascade Cycling Classic Criterium

Elite cycling returns to Bend's downtown streets for a full day of high-speed closed-loop criterium racing with tight corners, sprint finishes, and community excitement.

Arts & Culture
Once Upon a Mattress – Ponderosa Players
Ponderosa Players present the uproarious musical comedy based on 'The Princess and the Pea' at their intimate Bend playhouse.
Thursday, June 18, 2026 7:00 PM · Ponderosa Playhouse, 211 NE Revere Avenue, Bend
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Sports
Cascade Cycling Classic Criterium
Elite cycling returns to Bend's downtown streets for a full day of high-speed closed-loop criterium racing with tight corners, sprint finishes, and community excitement.
Sunday, June 21, 2026 · Downtown Bend
Old Mill District – Festivals & EventsCalShare
Outdoors & Active
Cold Plunge at Riverbend Park
A community cold plunge swim club gathering at Riverbend Park — a refreshing Sunday morning ritual open to all.
Sunday, June 21, 2026 8:00 AM · Riverbend Park, Bend
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Music & Nightlife
Tommy Emmanuel CGP – Living In The Light Tour
Legendary fingerstyle guitarist Tommy Emmanuel brings his Living In The Light Tour to the Tower Theatre for an intimate reserved-seating show.
Tuesday, June 23, 2026 7:30 PM · Tower Theatre, 835 NW Wall Street, Bend
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Festivals & Special Events
Bend Central District Block Party
The Bend Central District transforms into an open-street celebration with circus performers, aerial silks, interactive art, local artists, and community games for all ages.
Saturday, June 27, 2026 · Bend Central District, Bend
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Food & Drink
Spanish Wines & Tasty Tapas Tasting
A guided Spanish wine and tapas tasting event hosted by Central Oregon New Friends Connection — a great way to sip, snack, and socialize.
Saturday, June 27, 2026 6:00 PM · Bend
Meetup – Bend OR EventsCalShare
Date Night
GetUpandGroove DJ Set at Salud Restaurant
A live outdoor DJ set on the lawn at Salud Restaurant featuring feel-good dance tracks, movement, and community energy in the heart of downtown Bend.
Saturday, June 27, 2026 · Salud Restaurant, Bend
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