Ladies and gents, lace up your dirndls and buckle your lederhosen because there are three major events happening in just the course of three days. But don’t worry, we’re going to walk you through the weekend itinerary so you’ll know exactly how you want to plan it all out so you can get best of the trifecta!
Oktoberfest – Bend, Oregon
Beginning in the early 1800’s with a Munich Royal Wedding, Oktoberfest was born and has since grown as the largest folk and beer festival celebrated worldwide. To save you the hassle of traveling all the way to Germany though, Oktoberfest will return to Bend on Sept. 19 from 2-9pm, taking over the lawn outside the Deschutes Historical Museum in the heart of Downtown. Here’s what to expect:
Bark Bash at Oktober Fest
The Bark Bash event has rightfully been a crowd (and pup) favorite over the years spreading cuteness over the Bavarian festivities. Plus, all registration fees go directly to the Humane Society of Central Oregon which we consider a total win!
2pm – Weiner Dog Races
2:30pm – Running of the Bulldogs
3pm – Corgi Crush
3:30pm – Mutt Strut Dog Show
Games & Activities – 5-7pm
What would an Oktoberfest be without an array of quirky games to test your skills? Wrangle up your pretzel toss partner, muster up your strength for some good ol’ barrel rolling, and come dressed to impress because in all seriousness, there are some pretty awesome prizes up for grabs this year. Compete in the:
- Pretzel Toss
- Stein Holding Contest
- Beer Relay Race
- Beer Slide
- Barrel Rolling Race
- Costume Contest
- Yodeling Competition
Live Music: Accordion Club of Central Oregon – 7-8pm
Once the activities wind down and you’ve given it your all, it’s time to reward yourself for that performance of a lifetime in the yodeling competition. Kick back with a cold beer and enjoy some live music. Then, raise your stein and toast to Bavarian culture with a lineup of Oktoberfest favorites, including Paulaner Festbier, Hacker-Pschorr Oktoberfest Märzen, and Hacker-Pschorr Dunkel. After all that yodeling, barrel rolling, and celebrating, you’ve definitely earned it. Prost!
Oregon Whiskey Festival
Who doesn’t love award-winning whiskey? The sweet, woody, smoky aromas and flavors we crave during the fall season. Ahh, it’s like we can taste it now… and we’re in luck because the 2026 annual Oregon Whiskey Festival is happening all over again, taking place Sept. 18–19 at Oregon Spirit Distillers here in Bend.
Here, you’ll not only get to sip and savor the exceptional whiskeys being produced in Oregon but also celebrate the distillers whose passion maps the way straight to the treasure chest. Experiment firsthand with different mashed, fermented, distilled, and aged spirits, and learn more about the craft behind the bottle and how these makers create what we so gratefully get to enjoy.
Don’t forget to check out the VIP Admission Tickets, which will take your experience from top-notch to a true mastery of whiskey tasting. Enjoy an exclusive VIP evening on Friday, September 18, early access to Saturday’s event, a VIP lounge, and other fun amenities planned throughout the festival.
Participating Oregon Distilleries: 4 Spirits Distillery, 503 Distilling, Bendistillery, Bird Creek Distillery
Branch Point Distillery, Killdeer Distilling, McMenamins, New Basin Distilling Company, Oregon Spirits Distillers, Pilot House Distilling, Ransom Spirits, Vivacity and Westward Whiskey.
Bleachers with The Linda Lindas at Hayden Homes Amphitheater
Now, for the cherry on top, cap off the weekend with Bleachers and The Linda Lindas at Hayden Homes Amphitheater on Sunday, Sept. 20. Lead singer Jack Antonoff, famously recognized by his trademark thick-rimmed, round glasses, will bring this retro vibe to the stage not only with his iconic fashion sense, but with the band’s alternative indie rock sound that we hear is drawn from the one-and-only Bruce Springsteen. Some even say Antonoff has taken on the persona of Bruce Springsteen’s cooler, more chaotic cousin, though we’ll leave that up for the fans’ interpretation. Either way, Bleachers has an irreplicable sound of their own that can make any scenario feel like your own main-character moment, with a touch of heartache lifted by a euphoric feeling that can’t exactly be described. You really just have to take our word for it until you listen for yourself.
Bleachers’ vibe encompasses emotional catharsis and storytelling through lyrical brilliance, prominent saxophones, keyboards, and drums that sound great through your headphones and reach an entirely new level when experienced live. The band’s high energy, audience engagement, and poetic appeal are part of what draws in such a loyal fan base and affirms their 40+ sold-out shows, including their performance at Red Rocks Amphitheatre and their largest headline show at Madison Square Garden following the release of their 2024 self-titled studio album.
Supporting Bleachers is The Linda Lindas, bringing us some punk rock energy that takes us back to the early ’90s with influences from Riot Grrrl and a classic garage rock sound. The Linda Lindas have seemed to be playing the lay-low card, but really, they’ve been using the first half of 2026 to record and release their third studio album, “Gotta Get Out.” In late August, the album dropped and quickly gained recognition, especially the song “Closer,” featuring Hayley Williams, which has received critical acclaim.
And with Hayden Homes Amphitheater nearing its end of the 2026 concert season, we think this show is a great way to top it all off.
All in all, this weekend is stocked with some local fun for anyone looking for an opportunity to mingle and participate in community gatherings. Have fun, stay safe, be kind, and Prost to all!