John K. Gillespie
FALMOUTH – John K. Gillespie, 74, died peacefully on Feb. 13, 2026, surrounded by family. Born March 28, 1951, and raised in Calais, John was the son of Marian and Henry Gillespie.
He enjoyed a childhood full of friends, skiing, and Boy Scout activities, attaining an Eagle Scout Merit Badge. After a family move to Waterville, he met Cheryl Grant at a YMCA dance in 1967. John graduated from Waterville High School in 1969 and went on to University of Maine at Orono. John and Cheryl married in 1971 and graduated from UMO in 1973 and 1974, respectively. They moved to the Portland area for job opportunities. It became their home.
John found the craft and art involved in building rewarding and after learning from other builders, started his own business involving renovation. He worked with Portland Land Marks and refurbished townhouses. He later became involved in custom residential building with a specialty in historic reproductions. John and Cheryl raised their two daughters in one of his Greek Revival, center chimney capes in Falmouth. Through his career, J. Gillespie Builders created over 100 houses in the Greater Portland area.
John’s other life long passion was skiing. Over the years, he skied with numerous friends, and he particularly enjoyed skiing with his brothers-in-law Wayne and Steve. Later in life while in semi-retirement, John established a group of skiing friends at Sunday River Ski Resort, where he and his wife had a condo. He liked nothing better than sharing this favorite pastime with family and friends. A day on the slopes was always the “best day ever.”
John is survived by his wife Cheryl Grant Gillespie of 54 years; daughter Darcie Hohwald and husband Stephen, daughter Kelsey Gillespie; granddaughter Maya Hohwald; and several beloved family dogs and friends.
A celebration of life will be held on Feb. 28 from 1 to 3 p.m. at Brunos, 33 Allen Avenue, Portland, Maine 04105.
To share memories of John please visit, http://www.cascobaycremation.com
In lieu of flowers,
his family encourages donations to:
the American Cancer Society at
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