Experience the art of barrel-aging like never before at The 2025 Boss Mortgage Little Woody Beer, Cider & Whiskey Festival! Bend’s favorite beer festival returns to the Deschutes Historical Museum in downtown Bend on Labor Day weekend, August 29 and 30, 2025.
This year’s festival is going deeper into the woods — celebrating not only the art of barrel aging but all things tree-inspired. Think: juniper berry-infused ales, oak-aged stouts, pine needle brews and beers that quite literally root their flavors in the forest.
But the fun doesn’t stop with what’s in your glass.
For the first time ever, The Little Woody partners with the Bend Comedy Festival, bringing an evening of local laughs to the lineup on Friday night. Festivalgoers can enjoy the Locals Only Comedy Show from 6:15-7:30pm, included with admission, pairing perfectly with a pint of tree-forward beer or cider.
Gnomes, fairies and woodland wanderers are invited to show off their finest forest flair during Saturday’s Costume Contest. Prizes will be awarded for best gnome, best group costume and most creative forest creature. Whether you’re donning moss, bark, glitter or beard — this is your moment to shine.
VIP Admission begins at 4pm Friday and includes early entry, commemorative glassware, and access to a special presentation with 503 Distilling on the craft of canned cocktails — where innovation meets the spirit of the woods.
As always, The Little Woody supports the Deschutes Historical Museum, our host and beneficiary, with proceeds helping to preserve Central Oregon’s unique cultural heritage.
Event Details:
Friday, August 29 — 5-9pm
Saturday, August 30 — 12-9pm
Deschutes Historical Museum, Downtown Bend
Tickets & info: thelittlewoody.com
