Explore writers guides you to one of Central Oregon’s oldest parks, Redmond, along with younger sibling Madras and the esteemed DIY Sisters skatepark.

Redmond Skatepark

After Bend’s first Ponderosa Skatepark opened in 1997 (its second opened in 2014), Redmond was the next town in the region to secure a concrete skatepark. Built in 2001 by Oregon-based Dreamland Skateparks, Redmond Skatepark has endured surprisingly well over the past two decades. There have been plenty of advances in skatepark design in the interim, but Redmond’s features, including three bowls, snake run and street obstacles such as rails, are still serviceable and fun. That’s in part due to Dreamland’s regular visits to repair aging concrete and make small additions.

Madras Bike & Skate Park

OK, Madras is not exactly a sibling of Redmond, but it shares DNA from the same parent company, Dreamland, and has also endured well since its construction 16 years ago. The park has great flow, with a deep square-shaped bowl, smaller amoeba-shaped bowl and a small mini-bowl with a spine connecting it to the park’s street area featuring banks and wall ride. It’s a bit more of a haul, at least from points south, but Maras is always worth the drive. Bonus: Madras is thus far the only Central Oregon park with lights allowing for evening skating, perfect when the days are short and the nights are mild.

Sisters Skatepark

Arguably the crown jewel of Central Oregon skateparks, Sisters has three bowls, including a competition-size large bowl, a smaller pool reminiscent of the California backyards that spawned vertical skateboarding, and a small flow bowl and plenty of other quarter pipes and pump bumps to keep beginners and more street-oriented skaters rolling. It was designed and built in 2013 by skateboarders, who also raised funds and secured a grant from the Tony Hawk Foundation. The dream that led to the park’s construction continues today thanks to the Sisters Skatepark Alliance, a class at Sisters High School in which lucky students are working to raise funds and design and build more features, beginning with a concrete mini-ramp next year.