Constance Jane Trepania Montgomery, 96, of Lenox, passed away peacefully on November 3, 2025, just weeks shy of her 97th birthday.
Connie was born in Great Barrington in 1928, the daughter of Orville Morgen Trepania and Evelyn Haywood Trepania. In her early years during the Great Depression, she lived with her parents and paternal grandparents in Interlaken, Mass., where her grandparents owned the local general store and her grandmother served as the postmistress. The family later moved to Church Street in Stockbridge, to a home that remains in the family today.
Connie graduated from Williams High School in Stockbridge, where she excelled academically and played on a County Championship Girls Basketball Team. She began her career at Berkshire Mutual Fire Insurance Company, where she ultimately became the firm’s first female underwriter.
While working in Pittsfield, Connie met Max Montgomery, then a teacher and coach at Pittsfield High School. They married and, after living in New Jersey and Ohio, settled in Westwood, Mass., to raise their family. In retirement, Connie and Max returned to the Berkshires, first living in Stockbridge and, for the past 18 years, at Kimball Farms in Lenox.
Connie believed deeply in the importance of family and took joy in caring for those she loved. She also believed in the value of community engagement, volunteering in her children’s schools, at St. John’s Church, and at the First Congregational Church, and supporting a variety of local civic initiatives. While devoted to raising her family, Connie also found ways to contribute professionally as her children grew—preparing taxes at H&R Block and later working at BayBank. Always active and physically fit, Connie and Max shared a love of tennis, which became a centerpiece of their social life. She embodied a sense of conservatism and thrift—values rooted in her memories of the Depression and the collective spirit of wartime America. The loss of her brother Bud in the Korean War left her an only child, deepening her lifelong sense of responsibility and commitment to her parents and extended family.
Connie was predeceased by her husband of 59 years, Max Montgomery. She is survived by her four children: Jane (Tom) Brophy of Charlottesville, Va.; Anne (Rick) O’Connor of Eastham, Mass.; Kay (Glenn) Lammey of Simsbury, Conn.; and John (Suzie) Montgomery of Dedham, Mass.. She was a proud and loving grandmother to 12 grandchildren: Christopher (Lizzie), Michael (Liz), and Peter (Irene Shin) Brophy; Max, Campbell (Nick Eberhart), and Colleen O’Connor; Will, Katharine, and Grant Lammey; and Max (Abbey Cahill), Morgen, and Sam Montgomery. She also leaves six great-grandchildren: Eugene, Matilda, and Fred Brophy; Merritt and Paul Brophy; and Murphy Montgomery.
A funeral service will be held at the First Congregational Church in Stockbridge on Saturday, November 15, at 1:30 p.m. In lieu of flowers, donations in Connie’s honor may be made to the First Congregational Church in Stockbridge either directly or in care of Finnerty & Stevens Funeral Home, 426 Main St., Great Barrington, MA 01230. To send remembrances to her family, please visit the funeral home’s website.
Connie’s strength and resilience shaped those she loved. Her opinions were strong, her heart was generous, and her love—steady and unmistakable—anchored generations of family.
