Barbara Ann (Flaherty) Connolly, a cherished resident of South Portland, Maine, passed away on October 17, 2025, at the age of 91. Surrounded by family, she left behind a legacy of community service, dedication, and love that touched many lives. Her passing marks the end of a remarkable journey that began in 1933, when she was born to Barbara (Davis) and Andrew Flaherty.
Growing up in the Munjoy Hill neighborhood of Portland, Barbara was an active student at Cathedral Grammar School and Cathedral High School, where she served as President of the Class of 1951. A pivotal moment in her life occurred when her sister, Mary, introduced her to classmate Roger Connolly. The couple married in 1959 and enjoyed a joyful partnership that lasted for 66 years.
A Lifelong Commitment to Community and Family
In 1962, the Connollys settled into a home on Walnut Street, a welcoming neighborhood that became the backdrop for their family life. They raised two children, Michael and Maureen. Barbara’s commitment to education was evident through her involvement at the Frank I. Brown School. As a dedicated volunteer, she worked tirelessly to enhance both the school library and the community library, even serving as President of the Parent-Teacher Association.
Barbara was also an active member of Holy Cross Church, contributing significantly to the parish community. Her career included eight years at New England Telephone and Telegraph, and she later worked at two local daycares while raising her children. However, it was her time at the Warren Library and the South Portland Public Library, particularly at the Branch, that fulfilled her passion for books and people.
Barbara’s extensive network of friends and colleagues, including the “club ladies” and the “library ladies,” reflected her warm and engaging personality. She welcomed all who visited her home with open arms, always offering tea, food, and laughter.
Family and Legacy
Barbara is survived by her beloved husband, Roger Connolly, and their children, Michael Connolly of Lawrence, Massachusetts, and Maureen Connolly, along with her son-in-law, John Cunningham, of Pineville, North Carolina. Her family also includes nephews Stephen Mitchell and Dr. Timothy Mitchell, as well as her cousin, Anne Davis Griffin. Barbara took immense joy in her grandchildren, including Meghan Cunningham, Patrick Cunningham, and Kathryn Connolly, along with her great-grandchildren, who brought her boundless happiness.
Predeceased by her parents, her sister Mary, and brother-in-law Joseph Mitchell, Barbara’s spirit and faith were a source of strength for those around her. Her daily prayers served as a testament to her deep faith and commitment to family, friends, and even strangers.
In honoring Barbara’s memory, her family invites those who wish to pay their respects to attend visiting hours on October 22, 2025, from 16:00 to 18:00 at the Conroy-Tully Walker Funeral Home in South Portland. A Mass of Christian Burial will take place at 10:00 on October 23, 2025, at Holy Cross Church, followed by interment at Calvary Cemetery.
In lieu of flowers, the family suggests donations to the Ronald McDonald House of Maine or the South Portland Food Cupboard, both organizations that Barbara supported throughout her life. Her legacy of kindness and community service will continue to inspire those who knew her.
