Winn returned to Wells and became a teacher and cross country coach for
Wells High School. He continued running competitively, winning road races from Southern Maine to the South Shore of Massachusetts. Winn won the
Maine Marathon in 1982 and 1992, and the
Mid Winter Classic in 1994. He was the winner at the 1998 USA Masters Cross Country Championship at age 40. Winn and Sam Mills are the only two men to win both the
Maine Marathon and the Maine division of the
Beach to Beacon 10K. Winn coached track through 2017.
Wells High School administrators announced in 2021 that a $1,000 scholarship would be awarded to two Wells High School seniors each year in honor of Winn’s several-decade service to the school. In 2009, Winn was elected to the town of
Ogunquit Select Board, on which he served until 2020. == References ==