Winslow married Priscilla (Pat) May Whittemore on December 23, 1956, after two years' service in the United States Army. He went on to be a staff sergeant in the Army Reserves between 1956 and 1963.[1][3]
He began a career at Yarmouth Junior High School between 1956 and 1963, when it was located in Brickyard Hollow, teaching seventh-grade math and science.[4] Five years later, he became principal of grades 3 to 6 at Yarmouth Elementary School, and of Yarmouth Intermediate School between 1963 and 1968.[1]
Winslow was the fire chief in Yarmouth for seventeen of his forty-four years (1952–1996) in its ranks.[5]
He was a member of the Yarmouth Town Council for nine years, serving as its chair in 2006 and 2007. He received the town's "Latchstring Award" in 2014.[1]
Winslow was a Past Master of Casco Lodge #36 A. F. & A. M., Past High Priest of the Cumberland/Mount Vernon Chapter #1 R.A.M., a Knight Templar of Portland-St. Alban Commandery #2, a 32nd-degree Mason in the Valley of Portland, and a member of Portland Council #2.[1]
He was treasurer of the Yarmouth First Baptist Church from 2000 to 2016.[1]
On April 10, 2018, in their 62nd year of marriage, Pat died at the age of 86.[1]
Death
Winslow died on October 31, 2020, aged 89. He is interred, alongside his wife, in Yarmouth's Riverside Cemetery.[1]
What is now named Winslow Station, in his honor, served as Yarmouth's only fire station from 1953 until the mid-1990s. Located at 20 Center Street, it was used by the fire department until 2004.[6][1]