William D. McCalmon

YARMOUTH – William D. McCalmon, 84, passed away peacefully at his home in Yarmouth on September 20, 2026. Bill was born in Portland, Maine on October 18, 1941, the son of the late Irving and Lorraine (Daniels) McCalmon.

Bill grew up in Portland, living on Munjoy Hill and Peaks Island. A fixture at the Portland Boys Club, he discovered his lifelong love of swimming, which flourished throughout his years at Portland High School. Alongside his brother Irv, he dominated the Maine swimming scene and beyond, earning the nickname “The Mighty Macs” for their remarkable accomplishments. As captain of the Portland High School swim team, Bill set multiple school and meet records, won four Maine State individual titles, a New England high school title and went on to compete for the University of Connecticut. A 2024 inductee into the Maine Swimming Hall of Fame, Bill took great pride in his athletic accomplishments.

After college, Bill served as a medic in the Army National Reserves before embarking on a career in education and coaching. His kind heart and genuine love of children drew him to special education. After earning his master’s degree, he became principal of PREP, a school for children with special needs, and later served as Director of Special Education for the City of Portland. His dedication to children and their families left a lasting mark on the community.

In 1971, Bill met the love of his life, Mary Jane, at the Old Port Tavern. They married in 1973 and raised two children, Ryan and Sarah, with immense love and pride. His greatest joy was his family, especially his six grandchildren, who affectionately knew him as “Grumpy.”

A lifelong learner and true renaissance man, Bill eventually transitioned into the business world, working in sales, investments, and stock brokerage. His final and perhaps most beloved chapter was spent running the Long Island Store in Casco Bay for twenty years. There, Bill became a cherished island fixture, holding court daily with friends, family, and visitors, sharing stories, laughter, and his unmistakable gift for connecting with people. During those years, he rediscovered his passion for painting, transforming the store into an impromptu art gallery. His paintings found their way into the homes and hearts of countless visitors, many of whom still treasure his work.

Most know Bill as a tremendous golfer, always willing to play a round and give you some tips. He also loved fishing, painting, scuba diving, running, “old man poker”, reading biographies, and watching baseball. He especially cherished the many years he spent golfing and fishing with dear friends, most notably his lifelong friend Harvey Wheeler.

Bill’s greatest passion was his family, and his personal motto, “I’m ALL IN,” said everything about the way he lived. He showed up for as many games, practices, track meets, concerts, graduations, birthdays, holidays, and vacations as he possibly could. His greatest gifts were his time and presence – a joke to lift your spirits, a story to make you laugh, a hug when you needed one, or simply an attentive ear. He was his family’s biggest cheerleader and most devoted fan, right through his final weeks. His love, humor, generosity, and unwavering presence will be deeply missed and forever cherished.

Bill was predeceased by his sister, Elizabeth Tracy. He is survived by his beloved wife of 53 years, Mary Jane (Jacobs) McCalmon; his children, Ryan McCalmon and his wife Sarah Dodwell, and Sarah (McCalmon) Olivares and her husband Eric Olivares; his six grandchildren, Benjamin, Aaron, Nora, Asher, Camden, and William; his siblings, Irv McCalmon, Marie Guimont, and Jane Doyle; and many beloved extended family members.

A celebration of Bill’s life will be held Wednesday, November 4, 2026, at Ocean Gateway in Portland, Maine. Guests are welcome to arrive at 3:00pm, remembrances will begin at 3:30pm, followed by a reception until 6:00pm. In lieu of flowers, donations in Bill’s memory may be made to Barbara Bush Children’s Hospital online at: www.mainehealth.org/barbara-bush-childrens/giving-mainehealth-barbara-bush-childrens