WinterFest returns to Bend February 13th-15th, here’s what (and who) to expect
Kelsey Merison
Bend, Ore. (KTVZ) — Bend’s WinterFest is set to return February 13th-15th, 2026 in the Old Mill District. Here’s what–and who–to expect this time around.
Concerts are free with festival admission. At the Oregrown Main Stage, catch Brandi Cyrus, Tiffany, Saxsquatch, and Glass of Hearts – Blondie Tribute.
Attendees can expect ice carving demonstrations, a local market, a wine walk, a hot cocoa run and more!
Big Brothers Big Sisters of Central Oregon will be the beneficiary for this year. The festival is sponsored by Boss Mortgage Bend.
Here’s the full press release from Bend WinterFest:
“The 2026 Boss Mortgage Bend WinterFest returns to the Old Mill District February 13–15, 2026, bringing three days of live music, seasonal experiences, action-packed entertainment, and local flavor to thousands of festivalgoers.
HEADLINING MUSIC ACTS ANNOUNCED
Live music takes center stage on the Oregrown Main Stage, with concerts included in festival admission.
Friday Headliner: Brandi Cyrus (8:30–10pm)
DJ, creator, and multi-talented performer Brandi Cyrus brings her electrifying mash-up of country, pop, and electronic beats to kick off Friday night. Fresh off the success of her remix of Lainey Wilson’s Wildflowers and Wild Horses, Brandi’s high-energy style promises a dance-heavy WinterFest kickoff.
Saturday Headliner: Tiffany (8:30–10pm)
Pop icon Tiffany—who made history as the youngest female artist to top the Billboard charts—takes the stage Saturday night. Fans can expect a dynamic mix of her classic hits (“I Think We’re Alone Now,” “Could’ve Been”) along with her modern rock-leaning sound.
Additional Performances
Saxsquatch – Friday 7–8pmA 7-foot-tall sax-playing electronic producer delivering a unique, high-energy, genre-bending performance.
Glass of Hearts – Blondie Tribute – Saturday 7–8pmA New Wave-era tribute delivering the iconic sound and energy of Debbie Harry and Blondie.
Highlights of the 2026 Bend WinterFest include:
Ice, Fire & Light: WinterFest once again transforms the Old Mill District into a glowing winter wonderland. Watch talented ice artists turn massive blocks of ice into shimmering sculptures throughout the weekend. Beloved fire features return to warm hands and light up the night, creating WinterFest’s iconic mix of warmth, art, and spectacle.
Wonderland Marketplace: Discover a treasure trove of local and regional artisans showcasing handcrafted creations, from unique jewelry to woodworking and fine art. Plus, find the latest in snow sports apparel and outdoor gear at the Cascades Market, perfect for all your winter adventures.
Ollie Contest: The Pump Bump Jam Contest, one of WinterFest’s most thrilling draws, returns for 2026. With cash prizes, spectator-friendly viewing, and a dedicated rider community, the Pump Bump Jam continues to be a cornerstone of WinterFest excitement.
Wine Walk: A beloved kickoff tradition, the WinterFest Wine Walk returns Friday evening in the Old Mill District. Attendees will stroll through participating retailers while sampling wines from across the globe, enjoying exclusive in-store experiences and early access to WinterFest weekend.
Family Play Zone: Little ones can bounce, explore, and have fun with OMSI’s interactive brainteaser challenges and kid-friendly activities. A can’t-miss experience for the youngest winter enthusiasts.
Hot Cocoa Run: The Hot Cocoa Run 5K returns Sunday, Feb. 15, offering a fun, festive race with a full gourmet hot cocoa bar—complete with toppings and Crater Lake Spirits add-ins for adults.
The 2026 Oregon WinterFest continues its tradition of giving back, with a portion of proceeds benefiting a local nonprofit. We are proud to announce that Big Brothers Big Sisters of Central Oregon will be the beneficiary for this year. Big Brothers Big Sisters provides crucial mentoring to children in need of supportive role models, and the organization is contributing over 100 volunteers to make the event a success.
For more information, including vendor and volunteer applications and ticket purchases, visit our website at oregonwinterfest.com. Join us for the 2026 Oregon WinterFest, and let’s make this winter unforgettable!”