Phelps is now in his 13th season on the football coaching staff in 2019-20. He graduated from nearby Castleton University with a degree in sports administration and a minor in business. The Middlebury native will again coach the wide receivers in 2019. During the spring, Phelps has spent the last 14 years as an assistant coach for the Middlebury baseball team.
Phelps has also worked as an assistant coach with the Middlebury Union High School football team. During his time as a student at the 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 Shrine Maple Sugar Bowl for senior all-stars from both Vermont and New Hampshire.