A crowd at a concert, illuminated by bright lights, with people raising their hands and enjoying the performance on stage.

Fall 2025 Concerts and Happenings in Bend, Oregon

Published on September 1, 2025

Fall Festivals, Events, and Happenings in (and Around) Bend, Oregon | September & October 2025

As summer slips away and the air turns crisp, Bend comes alive with a fresh lineup of arts, entertainment, and seasonal celebrations. From rustic folk gatherings in Sisters to indie film premieres downtown and Halloween paddleboard parades on the Deschutes, this is your full guide to fall events in Bend this autumn, with something for every taste—whether you're after festivals, live music, or community fun.

Sisters Folk Festival | September 26–28 — Sisters, Oregon

Set in the scenic downtown of Sisters, this longstanding Americana fest spans multiple small stages. Expect roots, bluegrass, folk, and blues performances—even more intimate this year with artist-led workshops that elevate the sense of community.
Learn more & buy tickets

Cascade Equinox Festival | September 19–21 — Redmond, Oregon

Just a short drive away, this multi-genre festival pops with live music, interactive art, yoga sessions, and immersive installations at the fairgrounds. Family-friendly and deeply welcoming, it’s as much about experience as it is entertainment.
Learn more & buy tickets

Oregon Whiskey Festival | September 19–20 — Bend, Oregon

Taste your way through Oregon with whiskey samplings from over 20 distilleries, paired with gourmet bites and live music against crisp autumn skies. VIP perks include early entry and access to lounge areas.
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Bend Fall Festival | October 3–5 — Downtown Bend

Spanning six lively city blocks, this free, beloved autumn event features art vendors, a Harvest Market, kid zones, live bands, and craft beer and wine. Don't miss the “Great Bark Bash”—wiener-dog races, a Corgi parade, and pure cuteness overload.
Learn more & buy tickets

BendFilm Festival | October 8–12 — Various Venues Downtown

Indie film enthusiasts gather for five days of curated premieres, panel discussions, filmmaker Q&A sessions, and afterparties at downtown theaters and pop-up venues.
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Sisters Harvest Faire | October 12–13 — Sisters, Oregon

A longstanding tradition overflowing with artisan goods, live music, and seasonal eats. A perfect early-holiday shopping stop with handcrafted flair and mountain charm.
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Halloween in the Old Mill District | October 31 — Bend, Oregon

A family-friendly trick-or-treat crawl through the Old Mill District. Costumes encouraged for a festive stroll through shops and restaurants handing out candy—all in a fun, community-focused setting.
Learn more & buy tickets

Witches Paddle | October 31 — Riverbend Park, Bend, Oregon

One of Bend’s most iconic Halloween sights: paddleboarders costumed as witches take over the Deschutes River in a playful aquatic parade that’s equally spooky, scenic, and share-worthy.
Learn more & buy tickets

Other Fall Highlights & Community Events

  • Bend Farmers Market: Continues through October 8—perfect for fresh local produce, artisan goods, and casual strolling near Brooks Street Alley. More info
  • High Desert Museum: Remains a year-round cultural touchpoint with rotating exhibits and desert wildlife in naturalistic settings—ideal for a mellow fall day indoors. More info
  • Pumpkin Patches & Fall Farms: Local spots like DD Ranch and Smith Rock Ranch offer hayrides, petting zoos, corn mazes, and perfect seasonal photo ops all through October.

Stay with Riverhouse & Fall in Love with Bend

When the day winds down, Riverhouse offers the perfect place to warm up, settle in, and plan your next outing. With comfortable rooms, cozy firepits, and a riverside setting that shows off the beauty of the season, it’s an ideal match for fall travelers who want easy access to both nature and downtown.

You’re just minutes from the Old Mill District, walking distance to scenic trails, and a quick drive to festival venues, vineyards, and seasonal markets. Whether you're spending the day at the Bend Fall Festival, paddling in costume on Halloween, or catching the last of the autumn colors on a morning stroll, Riverhouse makes a welcoming, well-connected home base.

And because fall in Bend is full of spontaneous discoveries, having a central, comfortable spot to return to can make all the difference. Make your autumn weekend easy, memorable, and just the right amount of cozy. Make it Riverhouse.

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