Dylan Crossman grew up in Vermont skiing the tight trees of Mad River Glen, Sugar Bush, and Stowe. After high school, Dylan patrolled two seasons at Mad River Glen and participated in local ski competitions throughout the winter.
He won the Mad River Glen Triple Crown two years in a row and received a Telemark sponsorship from Rossignol. During the winter 99-00, Dylan took a trip to Alta to ski the Wasatch powder and has been coming back ever since. The next season he moved to Alta Ski Area to live and ski. Dylan skied in the U.S. Telemark Freeski comps in Jackson Hole and placed 2nd. For the next several years Dylan skied powder at Alta, backcountry lines in the Wasatch and competed in Telemark Freeski comps. From 02 to 07 Dylan dominated the Crested Butte Freeski Telemark National Champs, placing 1st five years in a row.
Disillusioned by the lack of support from sponsors in the free heeling world, Dylan turned to locking in the heel. In 2008, Dylan took 1st in the U.S. nationals Freeski Comp at Snowbird, becoming the first skier to win a telemark and alpine freeski comp consecutively.
The same year, dropping the knee in Sytrai, Austria, Dylan bagged the first decent of the anorexic "Crossman Couloir" on Loser Mountain. Intrigued by the first decent, he plans on doing more in the future.
Dylan spends his summers in Vermont working as an Arborist, and goes west when the snow starts to fly. It doesn't matter if he's free heeling or alpine shredding, he just enjoys being out there in the snow.