Wescott was born in Durham, North Carolina, and lives in Whistler, British Columbia.

Growing up, Wescott went to Mount Blue regional school district in Farmington, Maine.

Wescott attended Carrabassett Valley Academy where he studied and trained with fellow Olympians Bode Miller, Jeff Greenwood, Kirsten Clark and Emily Cook.

[5] Wescott, who started off the race in fourth, slowly advanced throughout the field until the end, when he narrowly defeated hometown favorite Mike Robertson on the final jump.

[6] Wescott co-owns The Rack, a restaurant and bar near Sugarloaf that caters food and drinks to skiers and snowboarders.