Donald L. Head

PORTLAND – Donald L. Head, 76, passed away with his family by his side on August 31, 2021, in Portland.

Don was a beloved husband, father, grandfather, brother, and friend, known for his deep commitment to civic engagement and philanthropy, his passion for music and art, his thirst for knowledge (nobody could beat him at Jeopardy), and his love of college football.

He grew up with his family in Point Pleasant, W.Va., graduating from Point Pleasant High School in 1962 as valedictorian, student council president, and a member of many other clubs and activities. He entered Denison University in the fall of that year and graduated in 1966 with a degree in economics while serving as president of the Denison chapter of Alpha Tau Omega fraternity. He remained lifelong friends with brothers of that fraternity and was “the glue” of their relationship.

Immediately after graduation he joined the management training program at the National City Bank of Cleveland. He was soon assigned to the investment research section of the Trust Department, beginning a 46-year career in investment analysis and portfolio management. After 12 years in Cleveland, he took a position at the Central Trust Company in Cincinnati.

Quite by accident, he and his family discovered the coast of Maine, and from 1972 on they returned almost every year, primarily to Islesboro. In 1982, they moved to Cape Elizabeth full time, and Don became head of portfolio management in the trust department of Casco Northern Bank in Portland, and later was named Senior Vice President. In 1989 he launched his own investment management company and with the contributions of a growing group of colleagues built the successful firm now named HeadInvest.

Signs of Don’s belief in philanthropy and volunteerism are evident all around Portland and the surrounding communities, from the cliff walk at Fort Williams, one of his favorite places in the world; to the Portland Observatory, where he was a docent who loved sharing his knowledge of Maine’s history; to Lincoln Park, where he has a bench honoring his service with the Friends of Lincoln Park; to Goodwill and Greater Portland Landmarks, where he was a board member; to the University of Southern Maine, where he served on advisory boards and supported the Promise Scholarship.

What he was best known for, though, was his love of music and travel. He sang in chorus groups early in his life and was a member of the Portland Community Chorus for many years later in life; he loved singing in the Magic of Christmas chorus. He was a board member and president of Opera Maine and a member of the USM School of Music Advisory Board for more than a decade. And he was a master whistler who could hit every note of the Dance of the Sugar Plum Fairy.

With his wife of 28 years, Caron Zand, he attended many art openings, and together they built a substantive collection of works from eminent Maine artists. They also traveled extensively throughout the United States, Europe, and the UK, often with family and friends, and took trips as far away as Africa and Turkey. When Don returned from each of their adventures, he started planning the next one, always looking for new places to visit as well as returning to their favorite places. Don called himself an Italophile, traveling to Italy 13 times and learning Italian in his 70s. And like his father, he loved photography, creating wonderful photo books from these extensive travels. Here at home, one of his favorite reasons to travel was to attend Marshall University football games with his siblings, both alums, and kids.

Don was predeceased by his mother and father, Doris Lambing Head and Clarence “Bud” Head.

He is survived by his wife, Caron Zand; his daughter, Amy Head Green, his son, Donald Alexander Head and daughter-in-law, Lari Bishop; his grandchildren Marshall Green, Peter Green, Harper Head and Gideon Head; his sister, Marjorie Head and brother-in-law, Mark Reid, his brother, Joseph Head and sister-in-law, Donna Head; and his former wife, Diane Pendleton.

Due to current health and safety concerns, the family has decided to hold a private celebration of life.

Arrangements entrusted to Hobbs Funeral Home, South Portland. Online condolences may be expressed at

In lieu of flowers, please consider a donation to Opera Maine or Greater Portland Landmarks.

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