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

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

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

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

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

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

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

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

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

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

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

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

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

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

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