Witches Paddle
Every October, the Witches Paddle takes over the Deschutes River with a colorful parade of costumed paddleboarders. Hundreds of participants dress in black hats, flowing capes, and other Halloween attire for a slow, scenic float through town.
Riverbend Park: About 8 minutes, 3.1 miles from Pioneer Park Rentals
FairWell Festival
The FairWell Festival brings together the top country artists for a full weekend of performances. Set at the Deschutes County Fairgrounds, the festival features both well-known headliners and up-and-coming talent. With wide-open skies and mountain views, it’s the kind of live music experience that feels as expansive as the landscape itself.
Deschutes County Fairgrounds (Redmond): About 17 minutes, 14.4 miles from Pioneer Park Rentals
Bend Design Conference
The Bend Design Conference gathers creative minds from across disciplines for a week of learning and collaboration. Artists, designers, architects, and entrepreneurs come together for talks, hands-on workshops, and interactive installations. It’s an inspiring mix of innovation, artistry, and community spirit—perfect for anyone who thrives on new ideas.
OSU-Cascades: 10 minutes, 2.8 miles from Pioneer Park Rentals
Munch & Music
During the summer, Drake Park transforms into Bend’s go-to spot for live music and local flavors. Munch & Music offers free weekly concerts alongside food carts, craft vendors, and activities for all ages. With its grassy lawns and Mirror Pond backdrop, it’s the ideal place to enjoy warm evenings and a variety of musical styles.
Drake Park: About 8 minutes, 0.9 miles from Pioneer Park Rentals
First Friday & Last Saturday Art Walks
Bend’s art walks invite visitors to explore galleries, studios, and creative spaces in a lively, social atmosphere. First Fridays highlight the downtown scene with exhibitions, live music, and complimentary refreshments, while the Last Saturday events focus on the Old Mill District and hubs like The Workhouse. Both evenings offer a great way to experience the city’s thriving arts culture.
Old Mill District: About 6 minutes, 2.6 miles from Pioneer Park Rentals
