Robert "Bert"

It is with profound sadness and heavy hearts that we announce the passing of Robert "Bert" Winslow, who peacefully departed this world in the comfort of his home on June 1, 2026, after a courageous battle with cancer. Born on September 23, 1937, in the picturesque town of Boothbay Harbor, Maine, Bert lived a life marked by love, service, and adventure. Bert was the beloved son of Cecil and Elizabeth (Lewis) Winslow and was raised with a deep appreciation for the natural beauty of Maine’s coast. He was predeceased by his first wife, Ruth M. Hartford, his cherished daughter, Jennifer C. Winslow, and his brother, Herbert A. Winslow. Despite these profound losses, Bert’s spirit remained unbroken, sustained by his faith and the love of his surviving family. In 1992, Bert found love again and married Confetti Maria, with whom he shared 34 wonderful years. Confetti was not only his partner but his anchor, providing unwavering support and companionship. Together, they cultivated a loving family, including his stepson Treb Iman, daughter Kate Winslow, and a host of grandchildren who brought immense joy to Bert’s life: Hannah Winslow and her husband Jude Alamo, Jessica Winslow, Holly Walton, and Madison Stilkey. Bert’s legacy also endures through his nephew Darren Winslow and his wife Kate, Scott Winslow, and his cousins Allen Winslow and his wife, Shawn. A proud graduate of Boothbay Region High School, Class of 1954, Bert’s early years were filled with academic achievements and sporting accolades. Following his graduation, he chose to serve his country with honor and distinction as a member of the United States Navy, a period of his life that instilled in him a sense of duty and camaraderie that he carried throughout his days. After his military service, Bert dedicated his professional life to the community he loved, serving as the East Boothbay Postmaster. His commitment to service extended beyond his career, as he was actively involved in the local community, always ready to lend a helping hand or share a warm smile. Bert was a man of many passions, most of which revolved around the great outdoors. He found peace and joy in sailing the waters that surrounded his home, golfing with friends, and hunting and fishing in Maine’s lush landscapes. These hobbies were not just pastimes but a testament to his enduring love for the natural world and the solace it provided him. In accordance with Bert’s wishes, a private funeral ceremony will be held, allowing his family to grieve and celebrate his life in an intimate setting. In lieu of flowers, the family kindly requests that donations be made to the United Methodist Church of Boothbay Harbor, an institution that held a special place in Bert’s heart. Robert "Bert" Winslow will be remembered as a devoted husband, a loving father, a doting grandfather, and a steadfast friend. His life was a testament to resilience, kindness, and the enduring power of love. As we say goodbye, we hold onto the cherished memories and the indelible mark he left on all who knew him. May he rest in peace, forever in our hearts.