Phelps is now in his fifth season on the football coaching staff after graduating from nearby Castleton State College with a degree in sports administration and a minor in business. The Middlebury native will again coach the wide receivers in 2011. Phelps has also spent the last five springs as an assistant coach for the Middlebury baseball team.

Phelps has also worked as an assistant coach with the Middlebury High School football team. During his time as a student at Middlebury High School, Phelps was a three-sport athlete, playing football, basketball, and baseball. His team won a state title with an undefeated season during his senior year, with Phelps taking part in the Maple Sugar Shrine Game for senior all-stars from Vermont and New Hampshire.