Cynthia Caldwell

Cynthia Caldwell, 63, passed away unexpectedly at her home in Shirley, Massachusetts on October 5, 2026. She was born on October 1, 1963 in Concord, Massachusetts, the youngest child of the late Malcolm G. Caldwell, Jr. and Carol A. Martin. Following her graduation from Acton Boxborough Regional High School in 1981, she continued her technical education, becoming a licensed HVAC technician and proud member of Pipefitters Local 537.

Naturally athletic, Cindy excelled in sports from an early age. She swam competitively and in high school she played varsity basketball, field hockey, and softball. A pioneer in girls’/women's ice hockey, Cindy played defense on the Waltham Wings, the A Division Senior Women’s team that won the National Championship in 1985. Affectionately nicknamed “Sam,” Cindy was a tomboy who loved to tag along with her older brother, Trip, and his friends, sharing his passion for the Red Sox, Bruins, and Patriots.

Cindy was genuine, caring, and fiercely loyal. She was the person you could always count on, ready to lend a hand whenever someone needed help. She was fun to be around, had a wonderful sense of humor and brought laughter and warmth to those fortunate enough to know her. She maintained strong, lifelong friendships and connected easily with people wherever life took her, whether it was visiting her Aunt Nancy in Wisconsin, at the Piccolino in Shirley, or simply going about her daily routine.

In addition to her parents, Cindy was predeceased by her beloved brother, Malcolm “Trip” G. Caldwell, III. She will be deeply missed by her sister Amy O’Leary and brother-in-law Jim, of Raleigh, North Carolina, her niece Blanca O’Leary and nephew John O’Leary of New Hampshire, her sister-in-law Beth Caldwell of Kennebunkport, Maine, as well as her aunts, uncles, cousins, and many dear friends.

Family and friends will gather to honor and remember Cindy for visiting hours on Thursday, October 22, 2026 from 4:00-7:00 pm at the Concord Funeral Home, 74 Belknap Street, Concord, MA. Her Celebration of Life will be held on Friday, October 23, at 11:00 am in Concord’s Colonial Inn, 48 Monument Square, Concord, MA. Burial will follow at Sleepy Hollow Cemetery, Concord.

Arrangements under the care of Concord Funeral Home, 74 Belknap Street, Concord, MA 01742  978-369-3388 www.concordfuneral.com