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
Enosburg 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 Enosburg 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 Enosburg
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, was the music minister at the United Methodist Church
and director of the Enosburg 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 travelled.
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, waterskiing, sailing, canoeing and
kayaking. He taught swimming and sailing at 4-H camps, and many
friends and family learned to waterski 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.