Malcolm G. "Trip" Caldwell III

Malcolm G. Caldwell III
"Loving Husband, Stepfather, Papi, Brother & Uncle"
Malcolm G. Caldwell, III, 62, of Waterbury, died peacefully on February 6, 2025, at VITAS Inpatient Unit at St. Mary's Hospital with his loving wife Beth (Mahaney) Caldwell and stepson Christopher Doyle by his side.
Malcolm, known affectionately to friends and family as "Trip" or "Mal" was born on March 20, 1962, in Concord, Massachusetts son of the late Malcolm G. Caldwell, Jr. and Carol Ann Martin. He graduated, in 1980, from The Lawrence Academy in Groton, Massachusetts, where he excelled in sports, especially hockey and football. He went on to attend the University of Vermont, earning a Bachelor of Science in Business Administration in 1984. While there he was a proud leader of Sigma Nu Fraternity and often spoke fondly of his time in Vermont where he made many lifelong friends.
Growing up in Concord and Acton, MA, Trip became an enthusiastic fan for all Boston sports teams and all things "Boston". He remained a loyal and devoted Bruins Hockey fan with whom he recently celebrated his 35-year anniversary as a tenured season ticket holder. Additionally, his passion for the Red Sox and Patriots was equally unmatched. He embodied the true definition of a gentleman – honorable, decent, and dedicated in all aspects of life. His engaging stories of travel, sports, family and friends will be cherished, as will his ever-present sense of humor. The energy and loyalty he displayed as a fan extended into his professional life, where he worked as an agency representative for Fidelity National Title Insurance Company for 20 years. He was a tireless advocate for his agents and took great pride in their success.
Trip met the love of his life, Beth, while on Cape Cod in the summer of 1996. They were married on September 11, 1999, on Goose Rocks Beach in Kennebunkport, Maine. It was love at first sight, and when they discovered they shared the same birthday, they knew it was meant to be. In later years, Trip traded his hockey sticks for golf clubs and skis where Beth was able to join him. Together they traveled countless times to ski resorts out West and to Canada pursuing their love for the freshest powder.
Besides his wife Beth of 25 years, he leaves to cherish his memory; two sons, Christopher Doyle (Stephanie Bennett) of Pompano Beach, FL and Jack Doyle (Tara Carver) of Essex, CT; four grandchildren who love and adore him, Charlotte, Jack, Haley and Hunter Doyle, two sisters, Amy O'Leary (James) of Windham, NH and Cynthia Caldwell of Shirley, MA; mother-in-law, Ellen C. Mahaney of Southbury, CT; brothers-in-law, Daniel J. "D.J." Mahaney (Lori Scappini) of Jupiter, FL and John D. Mahaney of Phoenix, AZ, many uncles, aunts, cousins, nieces, nephews and close lifelong friends that were by his side and supporting him during the last two difficult years of his life. He was predeceased by his father-in-law, Jack Mahaney, sisters-in-law, Meg Mahaney-Smith and Lisa A. Mahaney.
Trip's family would like to thank the Brookside Memorial/The Albini Family Funeral Home & Crematory for their support with local arrangements. Visitation will be held on Saturday, March 8th, from 10:00 to 11:00 a.m. at the Colonial Inn, 48 Monument Square, Concord, MA, followed by a blessing ceremony and celebration of life at 11:00 a.m., officiated by the Concord Funeral Home. The private burial will be in Trip's family plot in Sleepy Hollow Cemetery in Concord, MA.
Memorial contributions can be made in Trip's memory:
The Jimmy Fund 10 Brookline Place West, 6th Floor Brookline, MA 02445-7226