Newly engaged to be married and six weeks after enlisting in the Army Reserve in 1955, Sherwin was assigned to active duty in the military police in Okinawa, where he served for 17 months. Before heading to Japan, Sherwin completed his basic training at Fort Dix in New Jersey and his military police training at Ft . Gordon in Georgia. When he returned to the States, Sherwin continued his service in the Army Medical Reserve until his honorable discharge as a specialist in 1961, the same year he became a resident of Stamford.
For the next 41 years, Sherwin dedicated himself to teaching Social Studies in the Stamford Public Schools at Dolan Middle School, Stamford and Westhill high schools, and in the Alternate Routes to Success (ARTS) program. Sherwin earned his bachelor's degree in business administration from Long Island University; his master's in history from Teachers College at Columbia University; and his 6th year degree in education from Bridgeport University. Sherwin has been a volunteer for the Stamford Police Department and is a member of the Jewish War Veterans.
Sherwin and his wife, Betty, who he says taught for "only" 28 years in Stamford, raised two sons here, Ray and Bill, both of whom also reside in Stamford with their families. (The real reason Sherwin and Betty are still "up North.")