Deerfield cycling has deep roots and began as a competitive entity in the 1970s. After a brief hiatus in the early 2000s the team was reborn in the spring of 2008 as an interscholastic varsity team. A member of the New England Prep School Cycling League, the squad competes in a long-standing series of races throughout northern New England. From individual time trials and circuit races to traditional road races, the New England League tests all riders’ abilities. The Pioneer Valley provides an incredibly versatile training ground, with flat roads stretching north and south and steep hills surrounding campus to the east and west.

While Deerfield fields relatively small squads, the team has proven to be incredibly talented, with numerous podium finishes and stage wins. Historically, Deerfield cycling alumni have gone on to successful careers in cycling, including collegiate cyclists, domestic semi-pros, and a handful of professionals racing in Europe. Most importantly, Deerfield cyclists learn a strong sense of camaraderie and a love for the life-long sport of road cycling.

Freshman L. Holowesko leads a revamped squad during the 2015 season.  The team has high hopes for the Prep League race series and will ride to support Holowesko as he attempts to become the first freshman to win the overall Boy’s A division!

The future is looking bright for the team and if you are interested in joining a dedicated group of young athletes please contact Coach Calhoun at