Oregon WinterFest 2025

The Oregon WinterFest is a three-day festival that takes place every February on President’s Day weekend at the Old Mill District in Bend, Oregon. The event showcases Central Oregon creators, makers, and businesses. It features lots of entertainment, live music, delicious food and beverages from around the area as well as activities for children. No wonder the festival has long become a cherished winter tradition for thousands of locals and visitors.

Festival Attractions

Comes Oregon WinterFest, the picturesque Old Mill District turns into a beautiful winter wonderland. The location overlooks the Deschutes River. So, even if there is no snow, WinterFest is a great chance to celebrate everything about winter and enjoy what this season has to offer. The main attractions include holiday illuminations, ice carvings, fire pits with sculptures, and amusement rides. Light Art mesmerizes the public with the creative illumination from nationally recognized light artists. Wonderland Marketplace, Oregon Lifestyle Marketplace, and the Cascades Market offer arts and crafts galore. Also, the Royal Lounge is your best spot to grab a drink, relax, and enjoy the festival vibe.

Hot Cocoa Run (February 16, 2025)

Besides the cozy fire pits, you can also warm up at the Hot Cocoa Run, held on Sunday. As the name suggests, the participants will be rewarded with a full Hot Cocoa bar at the finish line, where you can treat yourself to toppings and Crater Lake spirits. For kids, the WinterFest has a separate competition—Kids Mini Marshmallow Run, held on Saturday.

2025 Lineup

On Friday, Crazy Train, a tribute to Ozzy Ozborne and Black Sabbath, will play from 8:30 to 10 pm. Crazy Train lead singer Tim Tugg's resemblance to Ozzy has fooled even the most hard-core of Ozzy fans. On Saturday night, the festival features a rap sensation Afroman with opening acts from The Bandulus and The Rusty Frets. Afroman performs from 8:30 to 10 pm. The Bandulus will perform from 7 to 8 pm, presenting a fusion of ska, reggae, and soul with a touch of rocksteady and R&B influences. Their Bandulus music is originates in classic Jamaican tunes while infusing it with a modern twist.

Ollie Contest

The Ollie Contest at Oregon WinterFest in Bend is a thrilling event for skateboarders to showcase their skills and push boundaries. Participants compete to achieve the highest and most stylish ollie—a foundational skateboarding trick. Held amid WinterFest’s lively atmosphere, the contest draws both locals and visitors, with spectators enjoying the display of talent, determination, and creativity. Skaters of all ages and skill levels are encouraged to participate, making it a family-friendly highlight of the festival's action-packed lineup.

Hours & Tickets

The festival hours are 5 pm to 10 pm on Friday, 11 am to 10 pm on Saturday, and 11 am to 5 pm on Sunday. General admission is $20. Youth admission is $12. Wine Walk Ticket is $30. More details on the schedule, the tickets, and updates are available on the event's official website.