Gertrude Carter

Gertrude “Trudy” Cleave Carter, 84, of Williamstown, MA, passed away peacefully on November 4, 2025, surrounded by her loved ones.

Born in Pennsylvania on August 26, 1941, Trudy was the eldest of three daughters of Howard and Barbara (Toy) Cleave. She spent her early years at her father’s Camp Champlain in Westport, NY, where she nurtured her lifelong love of music, swimming, and tennis.

A proud graduate of Duke University’s Nursing Program (Class of 1962), Trudy went on to earn her Master’s in Social Work from Smith College in 1976 after welcoming her two sons. Guided by a deep compassion for others, she devoted her career to human services and mental health. For nearly 30 years, Trudy served as a psychotherapist at Bennington College, where she was known for her warmth, insight, and unwavering dedication to her students. She became Coordinator of Campus Emergency Services in 1984 and later served as Director of Psychological Services for Students beginning in 1988. It was during this time that she met her life partner, Edward “Ted” Hoagland, with whom she shared a profound bond.

Trudy and Ted’s shared passions for animals, nature, and the arts shaped much of their life together. They enjoyed bird-watching, wildlife conservation, reading, writing, and traveling- especially their cherished summers in Barton, VT, near Lake Willoughby. After retiring from Bennington, they relocated to Martha’s Vineyard in 2005, where Trudy continued her service to others as a bereavement therapist for Hospice.

An avid gardener with an eye for beauty, Trudy expressed her creativity through her gardens, personal style, and home decor. Her sense of elegance, grace, and respect touched everyone she met.

Later in life, one of Trudy’s greatest joys was being “Granny” to her three beloved grandchildren. She delighted in their accomplishments and shared a special bond with each of them.

Trudy is survived by her sons Harvey “Trey” Carter III and his wife Cherie, of Pownal, VT, and Howard “Cleave” Carter and his wife Patricia, of North Adams, MA; her grandchildren Trey, Adrianna, and Croft Carter; her sister Bobbie and Boz Bosworth and their children Teal and Skye. She was predeceased by her younger sister Mary Cleave and former husband Harvey D. Carter II.

In lieu of flowers, the family requests donations to a wildlife conservation organization in honor of Trudy’s lifelong love of nature.

A Celebration of Life will be held on Sunday, November 23, from 1:00–4:00 p.m. at the Williams Inn in Williamstown, MA. Friends, family, and all whose lives she touched are invited to gather and share stories in remembrance of her remarkable life.