September Events in Central Oregon 2026

Every Wednesday in September

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

Every Saturday in September

• Northwest Crossing Farmers Market – Stroll the booths for farm-fresh food, crafts, and local treats in NW Bend.

Every Sunday in September

• Sisters Farmers Market – A small-town market filled with fresh foods and handmade goods.

September 2

• Music on the Green - Live music, local food & drinks, and craft vendors from 5:30-7:30 pm in Redmond
• Music on the Lawn & The Climbing Wall - live entertainment + climbing wall | Ages 4+ | $10 | Waiver required
• Geoffrey Louis Koch at Century Commons - Live music from 6-8 pm at Century Commons Taps & Trucks in Sunriver. Free to attend.

September 3

• Live music at The Lot - Rick Smith playing country/rock, blues, and funk at The Lot
• Dominic Fike at Hayden Homes Amphitheater - doors open at 6 pm. Show starts at 7:30 pm.

Labor Day Weekend in Central Oregon has a lot to offer. Here's the Labor Day weekend event lineup:

September 4-6

Bend Comedy Festival - three days of stand-up, improv, sketch, and late-night comedy in Bend

September 4

• First Friday Art Walk - Downtown Bend art walk with family activities and local vendor highlights
• Redmond First Friday Art Walk - meet with local artists while walking downtown Redmond
• First Friday Block Party - from 5:30-8:30 pm at The Commons Cafe & Taproom

September 5

• 10th Annual Sunriver Antique & Classic Car Show - from 10 am to 2 pm at The Village at Sunriver
• Summer Music Series at Mt. Bachelor - live music from 1 - 3 pm at the West Village Base Area
• Live Music at Century Commons - from 6 - 8 pm at Century Commons Taps & Trucks in Sunriver
• Summer Kickin' Concert Series: George Birge - at 5 pm at General Duffy's in Redmond

September 6

• Weird Al Yankovic @ Hayden Homes Amphitheater. Doors open at 5:30 pm. Show starts at 7 pm.

September 10

• Priday Ranch Tour - join the Deschutes Land Trust for a moderate 2-3 mile hike in Priday Ranch. Registration required.

September 12

• Santiam Wagon Road Walk - Join the Deschutes Land Trust for a moderate 3-mile hike at Wychus Canyon Preserve. Registration required.
• Forest Bathing - Slow down and reconnect with nature with a guided forest bathing session in the Metolius Preserve.

       Registration required.

• Paws & Pints - enjoy pop-ups and vendors with your four-legged friends from 12-3 pm in the Old Mill District.
• Discovery West PorchFest 2026 - neighborhood music festival with local food + drinks at Discovery Corner
• Forest the People @ Hayden Homes Amphitheater - Doors open at 5:30. Show starts at 7 pm.

September 13

• Nikki Glaser @ Hayden Homes Amphitheater - Doors open at 6 pm. Show starts at 7:30 pm.

September 18

• Riley Green @ Hayden Homes Amphitheater - Doors open at 4:30 pm. Show starts at 6 pm.

September 19

• Bend Oktoberfest - a high-spirited, family-friendly celebration in the heart of downtown Bend.
• Salsa on the Patio - Salsa music, dancing, great food, and good vibes at River’s Place Tap House + Food Carts

September 20

• Geology Hike - Join the Deschutes Land Trust for a geology hike at Aspen Hollow Preserve. Registration required.

September 22

• Dark Sky Party - Fall equinox - marvel at our incredible universe in the gorgeous setting of downtown Sisters, Oregon

September 25

• Geology Hike - Join the Deschutes Land Trust for a geology hike at Paulina Creek Preserve. Registration Required.
• 4th Friday Art Walk in Sisters - enjoy many different types of artistry while you experience the beauty of Sisters
• Food Cart Fridays - a family-friendly evening of food, live music, tasty beverages, and an outdoor Art Walk in Discovery West

September 25-26

• Sunriver Oktoberfest - a weekend of activities, food, games and more in beautiful Sunriver, Oregon

September 25-27

• Sisters Folk Festival  - multi-genre festival across 7 stages throughout charming Sisters, Oregon 

September 26

• Oktoberfest - German-style specials, plenty of beer and live music at McMenamins Old St. Francis School
• Sunriver Saturday Market - handcrafted items, local food and beverage items, and more!

September 27

• Sun Day Solar Fest @ Drake Park - games and activities, live music, educational materials, and more
• Geology Hike - Join the Deschutes Land Trust for a geology hike at Whychus Canyon Preserve. Registration required.
• Jack Johnson with special guest G. Love @ Hayden Homes Amphitheater. Doors open at 5. Show starts at 6:30 pm.

There are so many September events in Central Oregon to enjoy. Whether you are visiting Central Oregon to soak in the last of summer or you are here for a fall getaway, you can take advantage of everything this season has to offer including any of these special events.

Book Your September Stay In Central Oregon Today

There's still time to book your stay and visit Central Oregon before summer ends! Check out these properties with river access to pair iconic Central Oregon summer activities like floating the Deschutes River with these September events.