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14 Things to Do in Bend OR This Week · May 14–17, 2026

Top Picks This Week

Selco Pole Pedal Paddle

Bend's beloved 50th-anniversary multi-sport race combines skiing, biking, running, and paddling across a course stretching from Mt. Bachelor to Drake Park.

Fortunate Youth, Rubbah Tree & Nine To Fyah at Midtown Ballroom

A high-energy reggae triple bill hits Midtown Ballroom with Fortunate Youth headlining alongside Rubbah Tree and Nine To Fyah.

Music & Nightlife
Live at the Vineyard: Chance Mott
Local Powell Butte favorite Chance Mott plays an outdoor vineyard set paired with wood-fired pizza, award-winning wine, sangria, and beer.
Thursday, May 14, 2026 5:00 PM · Faith Hope and Charity Vineyards, 70450 NW Lower Valley Dr, Terrebonne
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Take It To The Limit - A Tribute To The Eagles
Moon Coin Productions brings a full Eagles tribute show to Tower Theatre with reserved seating and doors opening at 6:30 PM.
Thursday, May 14, 2026 7:30 PM · Tower Theatre, 835 NW Wall Street, Bend
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Wil Kinky @ Portello Lounge
Live music at Portello Lounge in NW Crossing featuring Wil Kinky for an intimate Friday evening set.
Friday, May 15, 2026 6:30 PM · Portello Lounge, 2754 NW Crossing Dr., Bend
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John Mulaney with Fred Armisen & Mike Birbiglia
Comedy superstar John Mulaney brings a stacked lineup including Fred Armisen and Mike Birbiglia to Hayden Homes Amphitheater for one night only.
Saturday, May 16, 2026 6:30 PM · Hayden Homes Amphitheater, 344 SW Selvin Hixon Drive, Bend
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Free Events
Thursday Night Live at Mountain Burger
Jenna Hansen performs live at Mountain Burger for a free night of great music, food, and community vibes.
Thursday, May 14, 2026 6:00 PM · Mountain Burger Bend, 2747 NW Crossing Drive, Bend
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Old Mill Classic Cruz
The 2nd Annual Old Mill Classic Cruz brings award-winning restorations, custom builds, and chrome craftsmanship along the river for a full day of classic cars.
Sunday, May 17, 2026 9:00 AM · Old Mill District, Bend
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Bend Farmers Market
The Bend Farmers Market is back every Wednesday 11am-3pm in Brooks Alley at Downtown Bend — local produce, food, and community.
Wednesday, May 20, 2026 11:00 AM · Brooks Alley, Downtown Bend
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Family-Friendly
Page to Screen: Dog Man
A free family movie screening of Dog Man presented by LaPine Elementary School, Assistance League of Bend, and Deschutes Public Library at Tower Theatre.
Friday, May 15, 2026 6:00 PM · Tower Theatre, 835 NW Wall Street, Bend
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Arts & Culture
Dragonfly Farm and Arts Open House
An open house at Dragonfly Farm welcoming visitors to explore local farm art and creative space in a serene outdoor setting.
Saturday, May 16, 2026 1:00 PM · 18270 Rock Springs Rd, Bend
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Helen Keaney & Shanan Kelley w/ Chelsea Woodmansee
National headliner Helen Keaney joins forces with Shanan Kelley and Chelsea Woodmansee for a night of sharp, coast-to-coast comedy at Tower Theatre.
Saturday, May 16, 2026 7:30 PM · Tower Theatre, 835 NW Wall Street, Bend
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Annie Elizabeth Presents: Positive Results Comedy Tour
Annie Elizabeth brings her Positive Results Comedy Tour to The Capitol in Bend for a Monday night stand-up show.
Monday, May 18, 2026 7:30 PM · The Capitol, Bend
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Outdoors & Active
Selco Pole Pedal Paddle
Bend's beloved 50th-anniversary multi-sport race combines skiing, biking, running, and paddling across a course stretching from Mt. Bachelor to Drake Park.
Saturday, May 16, 2026 · Mt. Bachelor to Drake Park, Bend
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Festivals & Special Events
Fortunate Youth, Rubbah Tree & Nine To Fyah at Midtown Ballroom
A high-energy reggae triple bill hits Midtown Ballroom with Fortunate Youth headlining alongside Rubbah Tree and Nine To Fyah.
Saturday, May 16, 2026 8:00 PM · Midtown Ballroom, Bend
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Food & Drink
Maison Kokoro French-Asian Pâtisserie Pop-Up
Chef Pâtissier Maya Howell's new Bend concept blends classic pastries like croissants and profiteroles with ube, yuzu, and mochi inside Pika Pika — a major upgrade to Bend's pastry scene.
Saturday, May 16, 2026 · Pika Pika, Downtown Bend
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