Our picks for the weekend include the first fall festivals, live music and more.
August 31 | Bend
A favorite among Bendites and visitors alike, Bellingham’s Polecat will perform at Crow’s Feet Commons on Thursday, August 31. The folk band has a unique sound that blends Americana, reggae and rock. The shows are always upbeat and high on energy. Catch them live for free in downtown Bend near Drake Park.
September 1 | Bend
First Fridays are one of the highlights of the month in downtown Bend. Businesses and art galleries stay open late, and the streets are filled with a cross section of locals and visitors eager to check out galleries that feature paintings, sculptures and jewelry, much of which is created here in Central Oregon. Add live music, free snacks and beer and wine tastings along the way and you’ve got the makings of a night on the town.
September 1-2 | Bend
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 takes place on the grounds of the Deschutes Historical Society in downtown Bend and features some of the most creative fermented concoctions from local and regional breweries, as well as the some of the best local food trucks. There will also be music on Friday and Saturday nights, including a performance from Boxcar Stringband on Saturday at 6:30 p.m. Tasting packages are $20 ($15 advance at bendticket.com) and include eight tokens and tasting glass.
Sisters Fall Street Festival
September 2-3 | Sisters
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 at this free event that is fun for families as well. Live entertainment throughout the weekend brings local and regional acts to town to celebrate the new season.
Updated August 30: An earlier version of this article included Pickin’ and Paddlin’. The event has been cancelled due to the smoke and has been removed from this list.