Cleo J. Surprenant, 96, of Dracut, died peacefully at his home on Friday, October 16, 2026. He was the beloved husband of the late Gloria (Francisco) Brown. They were married for more than 40 years, until her death in 2018.
Cleo was born in Winchendon on August 3, 1930, the eldest of eleven children of the late Frederick and Marcelina (Laferriere) Surprenant. He grew up and was educated in Lowell.
Cleo started working in the mills at a young age and soon became a supervisor at Paris Shoe, where he was floor manager for many years. He later worked as an assistant to the executives at Honeywell. In 1985 he bought the Highland Tap on Westford Street, and he owned and ran it for 25 years. Over the years he also managed several other bars and restaurants. He never really slowed down: he went on to tend bar at American Legion Post 87 until it was sold in January 2023, when he was 92.
At the Highland Tap, Cleo became part of the Cupples Square neighborhood, and to many people he was simply “the Mayor of Westford Street.” He always had a smile and a joke ready. He treated everyone who came through the door like family and gave plenty of good advice. In 2023 the City of Lowell gave him an official citation that called him “an icon of the Highlands.”
Cleo’s generosity reached well beyond the bar. For eight years he ran the Make-A-Wish Foundation Golf Tournament, which made dreams come true for many children. He also raised money for many other causes, including the Owl Diner Golf Tournament, Micky Ward Charities, the Salvation Army, Big Brothers Big Sisters, and the Boys & Girls Club.
Boxing was a lifelong love. Cleo was an active member of USA Boxing for more than ten years, working as a judge and a glover. He watched over Micky Ward throughout his career, and later over the young boxers who came after him. In his day he was also ranked among the top professional duckpin bowlers in New England.
He leaves his sons, Daniel Surprenant and his wife Helena of Michigan and Michael Brown and his wife Elyse of Dracut. He also leaves 11 grandchildren, many great-grandchildren, and his sister, Doris Santos of Tewksbury, his brother and sister in law Floyd and Patricia Ash of Westford. He was predeceased by nine brothers and sisters.
Celebration of Life: Cleo spent a lifetime bringing people together over a good drink and a good story. Family and friends are invited to celebrate his life at the Princeton Station in North Chelmsford on Thursday, October 29, 2026 from 4-8. Arrangements are by the McDonough Funeral Home.