Dorothy F. (Hogan) Hennessy, of Dennis, formerly of Milton, passed away peacefully on October 16, 2026. She was 89 years old.

Dottie is survived by her children, Stephen Hennessy (Tricia) of Milton, Susan Hennessy (Bridget) of Walpole, and Beth Hennessy Magann (Larry) of Canton; as well as by her grandchildren, Matthew, Caroline, and William Magann and Michael Hennessy. She was predeceased by the love of her life, her husband George Hennessy, as well as by her parents, William and Anna (McDonough) Hogan, and her sister, Anne (Hogan) Holmes.

Dottie grew up in the Hyde Park section of Boston before moving to Brookline as a teenager. She was part of a large extended family, and had happy memories of time spent with her many aunts, uncles and cousins. Some of her fondest memories were from summers at the family lake cottage in Halifax. She attended high school at Holy Cross Academy in Brookline, and was a proud graduate of Regis College.

In 1958, Dottie married George and they lived briefly in Charleston, SC while George was an officer in the United States Navy. They were happily married for more than 66 years. Dottie and George were best friends and shared a loving partnership. They raised their family in Milton, with summers in West Dennis on Cape Cod, where Dottie made life-long friends. In retirement, Dottie and George split their time between Dennis and Fort Pierce, Florida.

Dottie inherited a love of music from her father and played both the accordion and the organ. She had a beautiful voice and enjoyed singing in a choir in Florida. She was an avid tennis player, and enjoyed both golf and bridge. She gave her time over the years, whether it was being the school room parent or a scout leader, attending sports games, or shuttling kids in her station wagon. Friends were always welcome in her home and she loved getting to know all of them.

Dottie was selfless, patient, generous and caring. She looked out for others without drawing attention to it. She loved her family, and her many close friends who meant the world to her. Nothing made her happier than sharing life with those she loved – especially her four grandchildren whom she adored. She had a quiet strength and was an inspiration to all who knew her. She will be missed.

Visiting hours Saturday October 24th, 9:00AM – 11:00AM, at Dolan Funeral Home, 460 Granite Avenue, EAST MILTON SQUARE. A Funeral Mass will follow at 11:30 AM at Our Lady of the Visitation Parish, Saint Mary of the Hills Church, 29 Saint Mary’s Road, Milton. Burial will be private.