Frank Gennaro DeWolfe Sr.

Gray, ME- It is with great sadness we announce the passing of Frank Gennaro DeWolfe, Sr., a beloved husband, father, grandfather, great-grandfather, and friend, who left this world on April 8, 2025 at his home in Gray, Maine. Born on August 9, 1938, he was a man of charm, with a personality too big to be contained in just one lifetime.

Frank is now reunited in eternal peace with his cherished parents, James and Theresa (Susie), and his sister, Carolyn Brichetto — a comforting thought to the family who loved him so deeply. Though his presence here will be missed, the image of their heavenly reunion brings solace to those who remain. Frank will be deeply missed by his devoted wife of 66 years, Anna DeWolfe, whose love and partnership were the cornerstone of his life. Together, they built a vibrant family that was Frank’s greatest pride. Frank will be deeply missed by his 4 children and their spouses, 11 grandchildren and their partners, his 9 great-grandchildren, and of course his 2 adoring puppies.

A true Mainer, Frank grew up in Portland, where he met his beautiful wife, raised their family in Cumberland, and eventually retired to split time between Gray, Maine and Bradenton, Florida. Frank had a one-of-a-kind personality — big, bold, and brimming with humor. He could strike up a conversation with anyone, and charm their socks off. He had an uncanny knack for negotiation — most frequently walking away with the best deal. Whether making strangers or those he loved laugh or closing a tough deal, Frank knew how to leave his mark.

In his earlier years, Frank worked as a bus driver for Continental Trailways. A true man of the people, his passion and leadership led him to become President of the Amalgamated Transit Union, where he fought for workers’ rights. Frank’s entrepreneurial spirit also inspired him to open several ventures over the years, including Gennaro’s Mini Mart, a small mom-and-pop store; The Country Bumpkin, a local family diner; and a vintage Volkswagen Bug restoration business. True to his commitment to the working class, he made local news as the owner of Gennaro’s when he stopped selling instant lottery tickets in protest of proposed layoffs at the Maine Lottery Commission.

A proud Catholic Italian, Frank lived a long and happy life grounded in tradition, faith, and a deep love for his heritage. Throughout his life’s many chapters, Frank enjoyed good food, cooking, old cars, shuffleboard, boating, traveling with family to Hawaii, Peru, and Uruguay, discussing politics, and forever offering his opinion on any issue – big or small. Impressively, Frank grew and changed with the times, adapting to new technologies, and accepting changing societal times. But most of all, Frank cherished the company of his family and friends and knew how to fill a room with laughter. He was truly one of a kind, and he will be dearly missed by all who knew him.

Family and friends are invited to attend a time of visitation on Friday, May 30, 2025 from 4:00 pm to 7:00 pm at Jones, Rich & Barnes Funeral Home 199 Woodford St. Portland, Maine. A Mass of Christian Burial will be celebrated on Saturday, May 31, 2025 at 10:00 am at St. Peter’s Roman Catholic Church, 72 Federal St. Portland, Maine. Burial will follow at Pine Grove Cemetery in Falmouth, Maine.