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All Day

Sisters Folk Festival

Sisters Cascade Ave, Sisters

With the motto “All the town’s a stage,” the Sisters Folk Festival continues to entertain throughout the small town each year. The festival brings the best of Americana and folk music to Sisters, as well as highlights local acts that you’ll wish you had known about sooner. Various locations in Sisters. Grab your tickets here!

Ongoing

Sunriver Oktoberfest

The Village at Sunriver 57100 Beaver Drive, Sunriver +2 more

The 2025 Sunriver Oktoberfest is Sept. 26 and Sept. 27, marking a new tradition for the Sunriver community in Central Oregon. This inaugural event is part of a broader year of celebrations in Sunriver and will offer a festive atmosphere with a German theme. Come say "Prost!" with us over the last weekend in September...

Ring of Fire Mountain Bike Race at Wanoga Sno Park

Wanoga Sno-Park Cascade Lakes Highway, Bend

MTB event for 50 miles of Bend Singletrack to end the season! Part of the National Ultra Endurance Series Sports Register here to ride!

Oregon’s Largest Open-Air Garage and Vintage End of Summer Sale

Deschutes County Fair & Expo Center 3800 SW Airport Way, Redmond

We are back! Our event in June was so successful that we have been asked to host another one repeatedly. So, we are!! We have just gotten dates with the Deschutes County Fairgrounds to wrap up our Central Oregon Summer with another fun family-friendly sale on September 27th and 28th on the Buckaroo Lawn. There...

Cowdeo at Jefferson County Fair Complex

Jefferson County Fair Complex 430 SW Fairgrounds Road, Madras

Cowdeo Mission Statement-Providing an opportunity for kids ages 5 - 14 to experience friendly rodeo competition in a family atmosphere, while contributing to community non-profit organizations. Cowdeo originated in 1968 by the St. Patrick’s Catholic Church as a fundraising opportunity. In 2003, the Jefferson County Event Complex took over the fundraising event and turned it...

$5

Play Forever Mountain Clean-up

Mt. Bachelor 13000 SW Century Drive, Bend

The Play Forever Mountain Clean-Up Day is back again! On Saturday, Sept. 27, grab your sturdy hiking shoes, and head up to the mountain to help us collect litter before the snow flies. Here’s what you need to know: Registration is FREE and will be required to participate. Registration will be capped at 200 total...

Free

Oktoberfest at Boneyard Pub

Boneyard Brewery 1955 NE Division St, Bend

Join us for our 2nd Annual Oktoberfest celebration at Boneyard Pub, 9/27/25. Live music, food & beer specials!

Fresh Hops and Pop Up Shops

River's Place 787 NE Purcell Blvd., Bend

We are celebrating fall, fresh hop beers, local makers and live music. This is the best time of year! Shopping 12-5 pm Live Music 2-4 pm Fresh Hop Beers ALL DAY ~ Flights of 5 or 6 will be available from 12 pm-5 pm

Oktoberfest at The Grove

The Grove Market Hall 921 Northwest Mount Washington Drive, Bend

Come join us while Waypoint serves festive steins, music + food specials! Event is from 12-7 pm with live music going until 8pm.

Free

NICU Reunion 2025 at St. Charles

St. Charles Medical Center Bend 2500 NE Neff Rd, Bend

Members of the St. Charles Neonatal Intensive Care Unit family, including current and former patients and their families, and current and former staff, are invited to the St. Charles NICU reunion. The event will be held in Conference Rooms A-D (enter through Main Lobby). It will be a time to connect and celebrate with families...

Annual Yachtoberfest at Midtown Yacht Club

Midtown Yacht Club 1661 NE 4th St, Bend

Yachtoberfest is back for the 5th year! Come join us for food specials, festive beer, fresh hops, pumpkin cider, live music, vendors & fun! Prizes for the best Oktoberfest dressed!

Oktoberfest at McMenamins Old St. Francis School

McMenamins 700 NW Bond St.

Oktoberfest means celebration and beer - so we're serving up tasty German-style specials, plenty of beer and live music as a backdrop to it all. Property-wide food & drink specials...

Luscious Bend Food and Wine Experience at Mt. Bachelor Lodge

Mount Bachelor - West Village 13000 SW Century Dr., Bend

One night only. Three stories of immersive culinary magic. Join us for an unforgettable journey through flavor, connection, and creativity at Luscious Bend Food + Wine Experience — Central Oregon’s...

Bend Camerata at Fort Rock with Wanderlust Tours

Wanderlust Tours 61535 S Highway 97 #13, Bend

Join us for a night of art and stargazing in the Oregon Outback. Our adventure will start with a twilight hike through the stunning Fort Rock, an ancient volcanic tuff...