6 Things to Do in Bend OR This Week · October 15–18, 2026

Music & Nightlife

The War and Treaty with Blank Page

The War and Treaty performs at the Tower Theatre with opener Blank Page, presented by Tower Theatre Foundation.

Tuesday, October 20, 2026 7:30 PM · Tower Theatre

Date Night

Stella Heath: The Billie Holiday Project

Stella Heath performs The Billie Holiday Project at the Tower Theatre, a reserved-seating show in the 2026-27 TTF Season.

Sunday, October 25, 2026 7:30 PM · Tower Theatre

Outdoors & Active

Leaves Changing Colors & Sounds!

A Paulina Peak Social Club outing at Meadow Day Use, listed as a leaves-changing-colors event.

Sunday, October 18, 2026 9:15 AM · Meadow Day Use

Family-Friendly

Ice Skating at The Pavilion

Ice skating returns to The Pavilion, with skate sharpening offered on 10/8-9.

Wednesday, October 21, 2026 · The Pavilion

Arts & Culture

Under Western Skies by Sisters Festival of Books

Sisters Festival of Books presents Under Western Skies across multiple sessions through Sunday, October 25.

Tuesday, October 20, 2026 6:30-8 PM

Festivals & Special Events

Annual Pumpkin Patch + Fall Festival

DD Ranch's annual pumpkin patch and fall festival, with food carts, caramel corn, and caramel apples.

Weekends through Saturday, October 31, 2026 · DD Ranch, Terrebonne