A native of Georgetown, Massachusetts, Jon Pingree attended Governor Dummer Academy. He was awarded varsity letters in hockey (four), baseball (five), and football (three) while at Governor Dummer. On the ice, he was a two-time All-League selection and team Most Valuable Player, as well as the Flood Shield recipient as the League's MVP. He was also an All-League and team MVP pick once for football and twice for baseball. Before he graduated, Pingree earned the Goodwin Athletic Prize for the school's top male athlete.
Pingree entered Lake Forest College in the fall of 1981. During his four-year athletic career he earned eight varsity letters, including three in lacrosse, one in baseball, and four in his top sport of hockey. During his senior season of hockey, Pingree was named an All-American and selected team captain and Most Valuable Player. As the team's top defenseman, he helped Lake Forest to three straight NCAA Tournament appearances from 1983 to 1985.
After his graduation from Lake Forest in 1985, Jon entered the real estate business. He continued on that route until 1997 when he started his own small business - Greater Boston Autoware. He also coached hockey for a total of four seasons at Georgetown High School and Governor Dummer. He has been active in the Georgetown Athletic Association and the Georgetown Zoning Board of Appeals. Jon ranks his two children, Kristen and Thomas, as his greatest lifetime achievements.