Judith Anne Boland Caruso

Judith Anne (Mongrain) Boland Caruso, 85, a longtime Fairfield resident, passed away peacefully on August 17, 2026. She was one of three Mongrain children who grew up in Bridgeport, Connecticut. She attended Bassick High School and a few years after graduating, she met George Boland, Jr. of Fairfield. They quickly fell in love and started a family, raising six children in Fairfield.

Judy was loyal, creative and resilient. She believed in doing what you loved and what mattered. She encouraged her children to find their own paths, wherever those paths might lead. She was their greatest cheerleader and an unwavering source of support. Strong, honest, and fair, Judy had a good sense of humor to lean on when things didn’t go as planned.

Judy was a wonderful cook and a gracious host, known for the thoughtful and elegant gatherings she created for family and friends. She also was an excellent athlete, picking up golf and tennis in her late 30s.

A lifelong artist, Judy delighted in sketching pictures of her children. She also loved the beach, infants, horses, and every dog she met. Once her children were grown, she returned to art with new energy, exploring watercolors and oils. She was talented artist, exhibiting her paintings and winning several awards.

After moving to Florida with her second husband, Vincent Caruso, Judy worked and exhibited in several art galleries and studios. She loved painting alongside other artists and being part of a creative community.

Judy was a trusted advisor and devoted listener to her adult children. She was always willing to drive many miles to visit, celebrate, or simply be there when her family needed her.

Judy lived a life of selflessness and integrity. She spent her final days surrounded by her family. She will be deeply missed by all who knew and loved her.

Judy is survived by her children, Linda Boland (Jeff Wing), George Boland III (Jennifer), Michael Boland (Jana Tvedt), Susan Boland-Harter (Kevin Harter), Thomas Boland and Matthew Boland. Also, her grandchildren Megan Wing Chowdhury (Wes Chowdhury), Malia Wing, Sydney Boland, Kaitlyn Boland, Owen Harter (Kim), and Lillian Boland, as well as many nieces and nephews.

Judy was predeceased by her parents, Francis and Myrtle (Spencer) Mongrain, her siblings, Gerald Mongrain and Patricia (Mongrain) Leahy, and her first husband, George E. Boland Jr.

Judy’s family is deeply grateful to the devoted team at Meadow Mills Assisted Living who provided comfort and care in her final years, along with Enhabit Home Health and Hospice.

Family and friends are invited to remember Judy on Friday, September 18 from 4:00 - 6:30 p.m. at the Spear-Miller Funeral Home, 39 South Benson Road. A funeral mass will be held at 10 a.m. on Saturday, September 19 at St. Thomas Aquinas Church, 1719 Post Road, Fairfield, CT.