Stahley earned a Bachelor of Arts degree from Bridgewater State College in Bridgewater, Massachusetts in 1976. At Bridgewater State, he was a member of the varsity football and track teams. He earned a Masters in Educational Administration from the University of Massachusetts at Boston in 1981, and an additional thirty graduate credits in the field of K-12 Education. Stahley earned a Doctorate in Educational Policy, Research and Administration at the University of Massachusetts at Amherst in 2008.
Stahley lives in Brattleboro with his wife Gale. The couple have four children and four granddaughters. As a family, they are actively involved in the schools and community through co-curricular activities, youth recreational programs, and area service organizations.