Autumn Events Worth Traveling For
Fall in Redmond brings a few things. Crisp air, vibrant colors, and an authentic embrace and celebration of the season. From harvest festivals and craft fairs to pumpkin patches, parades, and live music under the stars, Redmond comes alive in autumn. Whether you’re here for a weekend or just a Saturday afternoon, fall events across the city offer cozy vibes, community fun, and a little something for everyone.
Take a look at everything happening this fall in Redmond, and start planning your next getaway to Oregon’s Basecamp.
September
- Thursday, September 11th: Live at the Vineyard: Jonathan Foster – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Friday, September 12th: Live at the Vineyard: The Backline Band – 6:00-9:00 pm | Faith Hope & Charity Vineyards
- Saturday, September 13th: Fanfest Summer Concert Series: Ramble On, Led Zeppelin Tribute Band – 7:00-10:00 pm | Blacksmith Public House
- Saturday, September 13th: Live at the Vineyard: Station Camp – 6:00-9:00 pm | Faith Hope & Charity Vineyards
- Friday, September 19th: Live at the Vineyard: Piano Flow Event with Paula – 6:00-9:00 pm | Faith Hope & Charity Vineyards
- Friday–Sunday, September 19th–21st: Cascade Equinox Festival | Deschutes County Fair & Expo Center
- Saturday, September 20th: Live at the Vineyard: Dry Canyon Stampede – 6:00-9:00 pm | Faith Hope & Charity Vineyards
- Thursday, September 25th: Live at the Vineyard: Eric Leadbetter Duo – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Friday, September 26th: Live at the Vineyard: Kurt Silva & Cynthia West – 6:00-9:00 pm | Faith Hope & Charity Vineyards
- Saturday, September 27th: Oktoberfest – Live music, German food, craft beer – 12:00-8:00 pm | Wild Ride Brewing
October
- Friday, October 3rd: Live at the Vineyard: Motel Kalifornia, Eagles Tribute – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Friday–Sunday, October 3rd–5th: Central Oregon Builders Association Home & Lifestyle Show | Deschutes County Fair & Expo Center
- Saturday, October 4th: Live at the Vineyard: Heller Highwater Trio – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Saturday, October 4th: Smith Rock Ranch Fall Festival Opening Weekend – 10:00 am–6:00 pm | Terrebonne
- Sunday, October 5th: Heaven Can Wait 5k 2025 – 10:00 am | Redmond High School
- Thursday, October 9th–11th: Sanctuary Barrel Race Fall Into Cash | Deschutes County Fair & Expo Center
- Friday, October 10th: Live at the Vineyard: Mango Stew – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Saturday, October 11th: Live at the Vineyard: The Substitutes – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Thursday, October 16th–18th: Columbia River Circuit Finals | Deschutes County Fair & Expo Center
- Saturday, October 18th: Southern Oregon Flea Market – 9:00–2:00 pm | Deschutes County Fair & Expo Center
- Saturday, October 18th: Live at the Vineyard: Brian Hanson Band – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Saturday, October 18th: Harvest Festival & Trick‑or‑Treat on 6th Street – 12:00–6:00 pm | Downtown Redmond
- Friday, October 24th: Live at the Vineyard: Grits n’ Gravy – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Friday–Saturday, October 24th–25th: Central Oregon Holiday Food & Gift Festival | Deschutes County Fair & Expo Center
- Saturday, October 25th: Oregon Guns and More Show – 9:00–5:00 pm | Deschutes County Fair & Expo Center
- Friday, October 31st: Halloween Bash with Live Music – 7:00–11:00 pm | High Desert Music Hall
- Friday, October 31st: Word of Victory Harvest Party – 5:00–8:00 pm | Deschutes County Fair & Expo Center
November
- Saturday, November 1st: Central Oregon Cards & Collectables – 9:00–4:00 pm | Deschutes County Fair & Expo Center
- Friday, November 7th–8th: Snowflake Boutique – 1:00–8:00 pm | Deschutes County Fair & Expo Center
- Saturday, November 8th: AMA EnduroCross – Doors open at 5:30 pm, show starts at 7:00 pm | Deschutes County Fair & Expo Center
- Saturday, November 8th: Fill Your Pantry (Farmers Market) – 11:00-3:00 pm | Deschutes County Fair & Expo Center
- Saturday, November 8th: Sip & Shop Holiday Market – 10:00 am–4:00 pm | High Desert Music Hall
- Saturday, November 15th: Wild Wild West Bully Show | Deschutes County Fair & Expo Center
- Saturday, November 15th–16th: Old Fashion Christmas | Deschutes County Fair & Expo Center
- Friday, November 14th: Live at the Vineyard: Kurt Silva & Cynthia West – 5:00-8:00 pm | Faith Hope & Charity Vineyards
- Friday, November 21st–23rd: Holiday Food & Gift Festival | Deschutes County Fair & Expo Center
- Friday, November 21st–23rd: Jurassic Quest | Deschutes County Fair & Expo Center
- Saturday, November 22nd: Southern Oregon Flea Market – 9:00-2:00 pm | Deschutes County Fair & Expo Center
- Thursday, November 27th: Redmond Turkey Trot – 9:00 am | Dry Canyon Trailhead
- Friday–Sunday, November 28th–30th: Holiday Village Market & Tree Lighting | Centennial Park
- Saturday, November 29th-30th: Annual Holiday Marketplace at the Vineyard – 9:00-4:00 pm | Faith Hope & Charity Vineyards
Come, Be a Part of the Action
Many events are free or low-cost, open to all, and bring that easygoing, small-town charm Redmond’s known for. Add in crisp high desert air, walkable downtown streets, and scenic views in every direction, and you’ve got the makings of a perfect autumn escape. Just be sure to plan ahead and book your stay early. Explore our lodging options now.
