Featured Events

Breweries, cideries and distilleries from around Oregon bring out the best of their barrel-aged brews for Little Woody. The annual festival is a celebration of all things barrel-aged, from beer and cider to whiskey. The event also has Bend’s favorite food carts on site and activities to entertain. Tickets start at $12. Deschutes Historical Museum.

Stroll through the Sisters Fall Street Festival and discover an array of local artists and craftsman. Local food and drink vendors will be on site. Live entertainment throughout the weekend brings local and regional acts to town to celebrate the new season. Free. Oak & Main Streets.

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. $50-$150. Various locations in Sisters.

Now in its thirty-fourth year, the High Desert Swap Meet is one of the most popular classic and antique car shows in the region. The one-day event is family-friendly and will have local food and drink vendors on site. Free. Deschutes County Fairgrounds & Expo Center.

Each September, find a little bit of Deutschland in Bend. Bend’s Oktoberfest takes over the downtown streets. With a (giant) stein in hand, taste a variety of beers from Bend and beyond. Local’s tip: If you volunteer to pour for a shift, you get to drink for free. $5-$28; cash only. Downtown Bend.

Twenty breweries from across the Pacific Northwest bring out their fresh hop beers for this annual event, not even in its eighth year. The family-friendly festival is a benefit for the American Cancer Society and will also have local food vendors and live music. $15 tasting package. Village Green Park.