New this year, the Bike Winter Park Weekend is a “choose-your-own-adventure” for the biking enthusiast. Roll Massif is hosting two signature events in Winter Park: Sunrise to Sunset and Crooked Gravel. All the participants need to do is choose between gravel and mountain, solo and team, and all day or 93 and 65-mile rides. All ages, all experience levels will take part in this high country bike event. 

The Sunrise to Sunset course capitalizes on two well-established strengths: the Sunrise to Sunset model and Winter Park’s deep mountain-bike roots. Ideal for a 12-hour relay format, the section of trails used in Sunrise to Sunset are just above town on the Rendezvous trail system, making access and relaxation between laps super easy. Winter Park Sunrise to Sunset will be held in conjunction with Crooked Gravel, so at day’s end, riders of both persuasions will be partying together at the Rendezvous Event Center. 

The 12-hour format is all about balancing camaraderie and challenge. Some folks will race it solo, but most choose to race in teams, from two-person up to five-person squads. As one teammate is out on course, banging out a 9.4-mile hot lap, the others are kicking back at camp, enjoying the festival atmosphere in the cool, high-mountain air. 

The Crooked Gravel courses are where high-altitude views abound in every direction. Both the 65- and 93-mile routes get right down to business, taking riders from downtown Winter Park onto remote gravel roads and up into the mountains. 

Brand new for 2019, Crooked Gravel takes a few cues from an exploratory event the legendary Ron Kiefel put together a decade ago called Crooked Roubaix. Back before gravel bikes were really a thing, Kiefel and some friends set out on a 95-mile dirt-road adventure from Winter Park up into the high mountains on road bikes. 

Fast forward to 2019 and gravel bikes are a thing. The two routes take in the very best of Grand County gravel, with long, winding climbs up through aspen and pine forests, wide open descents under the massive Colorado sky and – on the long route – some secret tracks never before explored in a cycling event. 

If nothing worth doing is easy, then Crooked Gravel is certainly worth doing… Both routes tackle over 5,000 feet of climbing on gravel, beginning in at 8,500 feet elevation. 

It’s all held in downtown Winter Park. Winter Park is a Rocky Mountain mecca for skiing and mountain biking, but only a select few know what an incredible place it is for gravel riding. Crooked Gravel will change that.

Riders will all set off en masse regardless of which route they are doing, how old they are, or how fast they want to go. This is how we Roll Massif. Once the timed segment on the climbing starts, riders who want to test their legs and their friends will power ahead, while those who would just prefer to go their own pace will settle in for the climb. There is no one right way to ride Crooked Gravel.

The event features a Free Concert Saturday August 10 at the Rendezvous Event Center, starting at 6:30 pm. Celebrate Bike Winter Park Weekend with Wildermiss, a Denver-based indie rock band, and, when you ride your bike to the venue, you’ll get half off your first beer (must be over 21)!

To learn more about the event, visit