Northfield, MA – It is with heavy hearts that we announce the passing of Christopher Bourne Shepard.
Chris was born in Rutland, VT to Anne Sheldon Shepard and Finley Jay Shepard, Jr. on September 6, 1944. He lived a full, impactful life as a transformative educator, musician, and cherished member of the Mount Hermon and Northfield communities.
Chris spent his childhood in Wallingford, VT before attending Avon Old Farms for high school, later returning to Rutland High School to complete his diploma. At Avon, headmaster Donald Winfield Pierpont inspired Chris to pursue a career in education. It was also during these formative years that Chris developed a lifelong passion for singing, playing guitar, and the Spanish language.
After high school, Chris married his high school sweetheart, Bonnie Wetmore Shepard, and they welcomed their first son, Todd. He matriculated at Castleton State College and St. Michael’s College before earning his undergraduate and master’s degrees from Middlebury College. During these years, Chris worked briefly on the General Electric assembly line and performed with John Peterson Folk Singers. He spoke fondly of his bandmates and loved sharing memories of meeting celebrities like sports broadcaster Al Michaels at the Summit Lodge at Killington Mountain.
Chris then began a distinguished 40-year career at Northfield Mount Hermon School (NMH), developing a deep appreciation for his colleagues and students. He was a passionate, kind, and patient teacher. He was famous in the classroom for bringing out his guitar to make Spanish come alive, often singing the Spanish alphabet to the refrain of Arlo Guthrie’s “Alice’s Restaurant” as well as Cuban classic “Guantanamera” made popular by Pete Seeger.
An avid traveler, Chris leapt at every opportunity to lead student trips to Spain, Mexico, and the Dominican Republic. Shortly after one extended trip to Spain, Chris and Bonnie welcomed their second son, Brendan “Shep.” On campus, Chris frequently brought his guitar to dorm duty and annual Mountain Day celebrations, gathering students together to sing classics like Don McLean’s “American Pie” and the Kingston Trio’s “Tom Dooley.”
Outside the classroom, Chris loved spending time with family, listening to the one Spanish station in Holyoke, MA, playing tennis on the clay courts at Mount Hermon, and learning new music. Though few realized it, Chris never learned to read music; he mastered every song entirely by ear, playing tape recordings repeatedly until he got each note right.
Following his retirement from NMH, Chris received a wonderful opportunity and joined his friend Dean Fusto on the Bement School’s trips to the Dominican Republic. He sang bass with the Keene Cheshiremen Chorus. Around town, many knew Chris as the man walking his beloved golden retriever, Logan, along Northfield’s Main Street. He was a familiar, friendly face outside the Northfield IGA, always ready to chat with friends, neighbors, and strangers alike. Between his walking and biking excursions, Chris shared his musical talents at the Northfield and Bernardston Senior Centers and remained an active member of the Northfield Trinitarian Congregational Church.
Chris spent his later years at RegalCare at Greenfield. His family extends their deepest gratitude to the RegalCare staff for their extraordinary care and compassionate support.
Leader of the Band
I thank you for the music and your stories of the road
I thank you for the freedom when it came my time to go
I thank you for the kindness and the times when you got tough
And papa, I don’t think I said I love you near enough
The leader of the band is tired and his eyes are growing old
But his blood runs through my instrument and his song is in my soul
My life has been a poor attempt to imitate the man
I’m just a living legacy to the leader of the band
– Dan Fogelberg
Chris will be dearly missed by his sons, Todd and his wife, Minnie and Shep and his wife, Stephanie; his grandchildren, Emily, Miles, and Tyler; his sisters, Laurie Shepard Coburn and Jaye Shepard Auer; his brother, Jan Shepard; and countless nieces, nephews, cousins, extended family members, former students, and friends.
A celebration of life honoring Chris will be held on Saturday, November 21, 2026 at 1:00p, at the Memorial Chapel on the Mount Hermon campus.
Kidder Funeral Home, 1 Parker Ave., Northfield, Ma. is assisting the family with arrangements.
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