September Events in Central Oregon

Tisha Kelly • August 28, 2025

September Events in Central Oregon

Your Guide to September Events in Central Oregon

September is one of the best times to visit Central Oregon—cool mornings, golden evenings, and plenty of events that celebrate the changing season. From live music and festivals to markets and outdoor adventures, there’s something for everyone this month. Here’s a look at what’s happening around Bend, Sunriver, Sisters, and beyond:

Every Wednesday in September

Bend Farmers Market – Fresh produce, flowers, artisan goods, and local flavors in the heart of downtown.

Every Saturday in September

Sunriver Saturday Market – Local produce, baked goods, art, and more at this fun community market.
Northwest Crossing Farmers Market – Stroll the booths for farm-fresh food, crafts, and local treats.

Every Sunday in September

Sisters Farmers Market – A small-town market filled with fresh foods and handmade goods.
Farmers Market at Worthy Brewing – Local vendors plus craft beer make this market a great Sunday stop.

September 1

Last Sunset Dinner at Mount Bachelor – Dine with panoramic mountain views at this special evening event marking the close of summer at Bachelor.

September 6
This is a busy day in Central Oregon with several events to choose from:

10th Annual Sunriver Antique and Classic Car Show – A favorite tradition, showcasing beautiful cars from past decades.
Sunriver Dog Fest – A celebration of pups with activities, vendors, and fun for the whole family.
Driven Through the Decades Car Show & Anniversary Party – More classic cars, food, and entertainment in Redmond.
Corey Kent at General Duffy’s Waterhole – Catch live music at this popular outdoor venue.

September 8

Heroes on the Run 5K Fun Run – A community run honoring local heroes.

September 11

Big Dill Pickleball Fundraiser – Play pickleball for a cause and enjoy the fun community atmosphere.

September 12

Sisters Festival of Books – A literary celebration with authors, readings, and community events.
Kidz Bop Live – A family-friendly concert with music kids know and love.

September 13

Bend Surf Fest – A celebration of river surfing and water culture in Central Oregon.
Stars Over Sisters Astronomy Starwatch – An evening under the stars with telescopes and astronomy experts.

September 16

Women Tasting Flights: Women Winemakers of Italy – A wine event highlighting female winemakers and their unique vintages.

September 19

Oregon Whiskey Festival – Taste and learn about some of the best whiskeys crafted in Oregon.

September 20

Cascade Equinox Festival – A multi-day celebration of music, art, and community.
Bend Oktoberfest – Traditional German food, beer, and music in downtown Bend.
Bark Bash at Oktoberfest – A dog-friendly addition to the Oktoberfest fun.

September 26

Paddle for a Purpose – A paddling event that raises funds for local causes.
Sunriver Oktoberfest Putt-Putt Golf Tournament – A playful mix of mini golf and Oktoberfest spirit.
28th Annual Sisters Folk Festival – A beloved music festival featuring singer-songwriters from around the country.

September 27