Douglas Macdonald, 83, longtime resident of Sheffield

In the 1980s he transitioned to his second career and true calling, receiving his MSW at Smith College and becoming a psychotherapist.

Douglas Cameron Macdonald, 83, longtime resident of Sheffield, passed away May 29 at Melbourne Place in Pittsfield with his family by his side.

Doug grew up in a small apartment in East Orange, New Jersey, with his widowed mother and his “Othermother,” Louise Jones. A brilliant student, he received a full scholarship to Princeton University. He went on to become an educator, earning a master’s degree in English at Rutgers and a doctorate in education from Temple University. He shared his love of literature as an English teacher and served as headmaster at several independent schools, including Oak Lane Day School, Germantown Friends School, North Shore Country Day School and Hammonasset School.

In the 1980s he transitioned to his second career and true calling, receiving his MSW at Smith College and becoming a psychotherapist. He worked at Main Street Human Resources in Great Barrington and had a private practice in Sheffield. He was deeply committed to the well-being of all his patients and maintained his practice up to the year before his death.

Doug adored nature. He hiked and camped with his daughter and with his students in the Smoky Mountains, the Green Mountains and White Mountains, and up and down the Appalachian and Pacific Crest trails. But his favorite slice of woodland was the 96 acres that was his home with Sherry, her pollinator gardens and a family of five bears. Over the course of their marriage, they shared their love with 13 dogs, five cats and too many songbirds to name.

Above all, he loved his wife. Doug and Sherry met when they were 4 and 3 years old respectively, when he and a friend rode their tricycles one block to her house and tied Sherry and her friend to a playhouse. After that auspicious beginning, they were high-school sweethearts, married during his senior year at Princeton, and shared 62 years of life’s ups and downs. He will always be with her in spirit.

He is survived by his wife, Sherry (Woolson) Macdonald; and his daughter Cameron Macdonald and son-in-law Robert Beattie. He was preceded in death by beloved son-in-law Gregory Williams.

Special thanks to the staff at the memory care unit at Melbourne Place for making it possible for Doug’s family during the pandemic.

Due to the coronavirus pandemic, a memorial service will be held at a later date. Condolences may be made through Birches-Roy Funeral Home in Great Barrington at Any of Douglas’ friends who wish to be notified of his memorial service can leave their email addresses in the condolences. In lieu of flowers, donations are encouraged to the Berkshire Humane Society or the Sheffield Land Trust.