Phelps is now in his 15th season in 2019-20 as an assistant baseball coach at Middlebury. He serves as the team's hitting and infield coach, while also coordinating the team's recruiting efforts. Phelps graduated from nearby Castleton University with a degree in sports administration and a minor in business. He played three years of baseball for the Spartans.
At the conclusion of the 2017 season, Phelps earned the New England Intercollegiate Baseball Association's (NEIBA) Kevin Burr Assistant Coach Award. The honor is presented to an active New England assistant coach who exhibits the integrity and dedication to the game of college baseball that Coach Burr demonstrated throughout his career.
Phelps has also worked as an assistant coach with the Middlebury High School football team. During his time 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 Maple Sugar Shrine game for senior all-stars from Vermont and New Hampshire.
The Middlebury native also serves as the wide receivers coach for the football team in the fall.