Worcester – Dennis A. Connole, 82, passed away on May 20, 2025, at UMASS Memorial Medical Center, University Campus. He leaves behind his beloved wife of 60 years, Joyce M. (Flynn) Connole; his son, Dennis A. Connole, Jr., and his wife Gayle; his daughter, Jill and her husband Ralph Streete, and his former son in law Mick Gambaccini; nine cherished grandchildren—Alexis and her husband Terrence, Dennis III and his significant other Naydelin, Sydney, Dominic, Samantha, Nichole and her significant other Dan, Jordan, Diana, and Melanie; and two adored great-grandchildren, Amelia and McKenna. He is also survived by his brother, Joseph Connole and his wife Maureen; his sister, Kathleen Senior and her life partner Don; and many nieces and nephews. He was predeceased by his siblings Richard “Rick” Connole, Maureen “Debby” Coakley, his brother-in-law Arthur, their son Brian Coakley and his daughter Jennifer Coakley Algieri.
Dennis was born in Worcester, MA, the son of the late Dennis J. and Mary (Palumbo) Connole. A proud veteran, he served his country in the U.S. National Guard during the Vietnam War Era.
After earning his Master’s Degree from Bridgewater State University, he dedicated his career to education, teaching biology for many years and finished his career as the librarian at South High School in Worcester, MA. A man of remarkable talent and boundless curiosity, Dennis was a published author, having written four books, the first of which was on the Nipmuck Indians in which he was considered one of the foremost experts. He was working on a fifth book at the time of his passing.
Dennis had a lifelong passion for racing and restoring cars, he proudly owned a 1960 Ford Starliner. He was the founder of the Valve Burners car club where he led a group of passionate car lovers who enjoyed racing and showcasing their vehicles. He regularly attended and competed in car shows, spending countless hours perfecting his beloved car alongside his son—an experience that combined craftsmanship with meaningful family time.
His love for music was ever-present. He had a passion for music and often performed with his guitar, both at home and at local restaurants all around central Massachusetts and Florida bringing joy to all who listened or serenading his family at home, his music brought people together and made memories shine.
One of Dennis’s greatest joys was caring for the family’s log cabin in The White Mountains, New Hampshire, a peaceful retreat he maintained with love and dedication. He spent countless hours tending to its upkeep, making sure it remained a warm, welcoming place for all. Surrounded by gardens bursting with flowers of every kind, the cabin reflected his deep appreciation for nature and beauty. Each summer, the cabin came alive with family gatherings—fishing, music, laughter, and quiet moments on the porch. It was a place where memories were made and love was always present, thanks to the care and heart Dennis put into every detail.
In the winters, Dennis and Joyce enjoyed their time in Daytona Beach, Florida, where they relaxed by the ocean, explored local spots, and cherished peaceful moments together enjoying the sunset by the pool.
Dennis’s greatest joy in life was being a grandfather. Affectionately known as “Boppy” by his nine grandchildren and two great-grandchildren, he embraced the role with his whole heart. He was a constant source of love, laughter, and wisdom—always ready with a story, a song, or a camera to capture the moment. Whether it was helping with school projects, sharing life lessons, or simply spending time together, his grandchildren were the light of his life. The bond he shared with each of them was deep and special, and the love he gave so freely will be carried in their hearts forever.
Above all, Dennis was known for his generosity, kindness, and wit. He quietly supported people in need throughout his life, never seeking recognition, only aiming to help. As a teacher, musician, writer, photographer, and mentor, he left a legacy of love, learning, and laughter that will live on in all who had the honor of knowing him. He shared 60 years of wedded bliss with his beloved wife, Joyce—a partnership filled with love, adventure, and unwavering devotion. All services will be private.
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