Jay Allen Sheperd, 86, died peacefully on July 14, 2025, following a brief illness. He was born to James and Viola (Halliday) Sheperd in Mount Vernon, N.Y. Jay and his sister, Penny (Wright), grew up in Enosburgh, Vt., and on Lake Carmi. He graduated from Enosburg Falls High School and the University of Vermont.
Jay was a music teacher in the Bradford and Enosburgh schools, owned Windemere Farm, and, after retiring from farming, did carpentry work throughout Franklin County. When Jay traded teaching for farming, he maintained an active role in education by serving on the Enosburgh School Board and, especially, by being a mentor to many young people who were employed on the farm where he raised veal calves and Highland cattle and always had a Great Dane by his side.
Music was part of Jay’s whole life; he was a member of the Vermont Music Educators Association, served as state secretary, and was selected to serve on the Professional Rights and Responsibilities Committee of the Vermont Education Association. In addition to teaching band and vocal music, he was a bass soloist in the Champlain Chorus and North Country Chorus, the music minister at the United Methodist Church, and director of the Enosburgh Community Chorus. He found great enjoyment in arranging choral music and then hearing the arrangements performed. He and Martha fell in love with bluegrass later in life. They passed many happy winters touring to bluegrass festivals throughout Florida, Alabama, Mississippi and Louisiana in their fifth-wheel camper, making new friends and kayaking the creeks, rivers and bayous as they traveled.
Jay was a member of the Green Mountain Club and maintained much of the northern section of the Long Trail. He loved boats and spent his summers on the water swimming, water-skiing, sailing, canoeing and kayaking. He taught swimming and sailing at 4-H camps, and many friends and family learned to water-ski behind his boat on Lake Carmi. Jay was also a competitor in the Great Race Triathlon in St. Albans Bay for 25 years, taking on the canoeing portion of the race for his team, the “Bay Day Originals.”
Jay married Barbara Williams in 1967, and they had three children, Anne, Sarah and Jonathan. In 1984 he married Martha Gehrke and gained two more children, Jody and Amie. Jay loved spending time with family and was a beloved grandfather to Nathan, Sam, Mariah, Javin, Avery, Paige, Hunter, Nicholas, Will, Micha and Phoebe and great-grandfather to Carter, Cade and Desmond.
Jay will be remembered for his integrity and kindness and for being a champion at “resting his eyes” in his favorite chair.
A celebration of Jay’s life will be held at the convenience of the family. In lieu of flowers, donations may be made to the Green Mountain Club or Vermont Public Radio.
Condolences, photos and favorite memories may be shared through gossfs.com.
This article appears in Jul 16-22, 2025.