Colorado Upstart Roll Massif Launches 2 Gravel Events for 2019

New American Sportive series includes road, gravel and MTB

Roll Massif is a new collection of eight road, gravel and mountain bike sportives across the state of Colorado. On the gravel front they promise two impressive sportives including Wild Horse Gravel in De Beque and Crooked Gravel in Winter Park.

The organizers promise an immersive community experience in some of the most beautiful parts of Colorado. Destinations include the Colorado National Monument, Castlewood Canyon State Park and Winter Park.

Our road, gravel and mountain bike sportives offer the perfect balance of camaraderie and challenge. With timed segments and varying options of distance and difficulty, Roll Massif sportives are fun for riders new and old.
— Co-founder Chandler Smith

Wild Horse Gravel 

  • Event: Wild Horse Gravel

  • Date: MAY 11, 2019

  • Location: DE BEQUE, CO

Brand new for 2019, Wild Horse Gravel showcases the unique high desertscape of the Western Slope. Hosted on the luxury High Lonesome Ranch, riders will be treated to a country cook-out, campfire, cabins, camping – or glamping – and the best local music. In short, there will be a Colorado country party to accompany the ride.

In addition to being hidden well, well off the beaten path, The High Lonesome Ranch simply isn’t open to riding year-round, so participants benefit from exclusive access to this secret stash of top-shelf gravel. You’ll only be disappointed if you were hoping for a bunch of auto traffic on the route…

We have two routes to choose from, and riders can decide which one on the day – even mid-ride. Feeling strong? Go long. Feeling like 50 miles is plenty? Totally your call.

Held early in the season, Wild Horse Gravel seeks to blow out the cobwebs and blow riders’ minds with a full spread of gravel terrain. There will be timed segments that riders can take as seriously or as frivolously as they like — the name of the game is doing a big gravel ride with friends new and old. Even those that hammer away at maximum speed will stop to regroup, taking in the views and the delicious local goodies at the well-stocked feed stations. As with all Roll Massif Sportives, you’re going to want to bring your camera.

Crooked Gravel

  • Event: Crooked Gravel

  • Date: AUGUST 10, 2019

  • Location: WINTER PARK, CO

High-altitude views abound in every direction. Crisp mountain air exhilarates the senses. And swarms of riders fire each other up. And that’s before the ride even starts!

Both the 68- and 97-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. Our 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 Team

Co-founders Chandler Smith and Scott Olmsted have a combined 30 years experience putting on the biggest cycling events in Colorado. Robin Thurston serves as an investor and adviser to Roll Massif. Event veterans Liz Brown and Tracy Powers join cycling media veterans Nick Ramey and Ben Delaney in rounding out the team.


Registration for all eight Roll Massif sportives is open now on Riders who want to save time and money can buy a Pedal Pass for multiple events. The Pedal Pass comes in 3-Pack, 4-Pack, VIP Pass and Massif Pass options.

Roll Massif will also have two 12-hour mountain bike races, Sunrise to Sunset Elephant Rock and Sunrise to Sunset Winter Park. Kids 18 and under ride free in the six road and gravel sportives. 

For more information visit Roll Massif