South Portland Mourns the Loss of Community Pillar Barbara Connolly

Barbara Ann (Flaherty) Connolly, a cherished resident of South Portland, passed away peacefully on October 17, 2025, in Pineville, North Carolina, surrounded by her family. She was 91 years old. Born in 1933 to Barbara (Davis) and Andrew Flaherty, Barbara grew up in the Munjoy Hill neighborhood of Portland. Her early education included attending Cathedral Grammar School and Cathedral High School, where she became President of her graduating class in 1951.

Barbara’s life took a significant turn when her sister, Mary, introduced her to a classmate, Roger Connolly. Their connection blossomed into a marriage in 1959, leading to 66 years of companionship. Together, they created a loving home on Walnut Street in South Portland, where they raised their two children, Michael and Maureen.

A Lifelong Commitment to Community and Education

Barbara was deeply committed to her community. She dedicated countless hours to Frank I. Brown School, focusing on enhancing both the school library and the community library. Her leadership as President of the Parent-Teacher Association was instrumental in fostering a collaborative environment for students and parents alike.

As a devoted member of Holy Cross Church, Barbara actively contributed to parish life. She worked for eight years at New England Tel and Tel before transitioning to roles at local daycares while raising her children. Her career culminated at AAA of New England and later at the Warren Library and the South Portland Public Libraries, particularly the Branch, where her passion for literature and connection with people flourished.

Barbara is survived by her beloved husband, Roger Connolly, and their children: son Michael Connolly of Lawrence, Massachusetts, and daughter Maureen Connolly, along with son-in-law John Cunningham of Pineville, North Carolina. She is also survived by her nephews, Stephen Mitchell and Dr. Timothy Mitchell, as well as her cousin, Anne Davis Griffin.

A Legacy of Love and Generosity

Barbara’s family includes her cherished grandchildren: Meghan Cunningham, Patrick Cunningham, and Kathryn Connolly, along with her grandniece and grandnephews. She found immense joy in her great-grandchildren, Roger and Clara Takach, whose smiles brightened her days.

Predeceased by her parents, sister Mary Mitchell, and brother-in-law Joseph Mitchell, Barbara left a lasting legacy of faith and joy in living. Her unwavering dedication to her family was evident through her daily prayers for loved ones and even strangers. Barbara’s friendships enriched her life; she was surrounded by the “club ladies,” “library ladies,” and fellow members of her prayer groups.

Barbara and Roger’s home was a welcoming haven, known for its warmth, where friends and family gathered often for tea and laughter.

Visitation for Barbara will occur on October 22, 2025, from 16:00 to 18:00 at the Conroy-Tully Walker Funeral Home, located at 1024 Broadway in South Portland. A Mass of Christian Burial will be celebrated at Holy Cross Church on October 23, 2025, at 10:00, followed by interment at Calvary Cemetery in South Portland.

In lieu of flowers, the family requests donations be made to the Ronald McDonald House of Maine or the South Portland Food Cupboard, both of which Barbara supported throughout her life. To view Barbara’s memorial page or leave a condolence, please visit http://www.ConroyTullyWalker.com.