Jane McCaffrey

Jane McCaffrey, age 83, of Westfield, Chelmsford, and Waterville Valley, passed away peacefully on July 26, 2026. She is survived by her brother, Peter McCaffrey, his wife, Roxanne, and their son, Conor; her sister-in-law, Theresa McCaffrey, widow of her late brother Frank McCaffrey, and their sons, Michael and his wife, Rebecca, and Christopher; and by Nancy McCaffrey, the wife of her late brother, Thomas McCaffrey. She was predeceased by her parents, Thomas and Ruth McCaffrey; her brothers, Frank and Thomas; and her niece, Colleen.

A celebration of Jane's life will be held on August 14 at St. Mary’s Church, 25 North Rd, Chelmsford, MA. Family and friends are invited to gather beginning at 10am followed by a Mass of Christian Burial at 11am.

In lieu of flowers, memorial donations may be made to the Waterville Historical Society or to the charity of one's choice in Jane's memory.

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Jane grew up in Westfield, Massachusetts, the adventurous eldest sibling among three younger brothers. She graduated from St. Mary's High School before earning her bachelor's degree in teaching from Elms College and, later, a master's degree in education from Lesley University.

After graduating from Elms, Jane was offered a first-grade teaching position in Billerica, prompting a move to Roslindale. She would go on to spend 37 years teaching first grade at the Dutile School in Billerica, and made her home in Chelmsford for the next 40 years. Jane's impact on her students ran deep and lasted for decades. Generations of Dutile families and colleagues fondly remember her as one of the kindest, most dedicated teachers their children ever had, and someone who made every student feel included and capable. Among her own favorite memories was a surprise party her class threw her on her 50th birthday, and the deep satisfaction of teaching one of her special needs students to read.

An avid outdoorswoman, Jane loved hiking, tennis, and skiing, and enjoyed wood carving and gardening as hobbies. She spent many winters in Waterville Valley, New Hampshire, skiing with colleagues who became dear, lifelong friends who she cherished as a second family. She also taught many family members to ski over the years with patience, expertise, and humor. After retiring, she moved to Waterville Valley and continued creating deep friendships with the community there. She joined the Silver Streaks ski club, and was often found tending the gardens throughout the Valley. She traveled extensively as well, with memorable trips through Ireland, Germany, and Austria, and throughout the United States.

Jane was also a founding member of the Waterville Valley Historical Society, where she helped organize the town's collection, worked on exhibits in the Society's "Little Museum," and volunteered as a historical trolley guide. Closer to home, she had a soft spot for the chipmunks living nearby, who would happily eat peanuts from her hand on the deck.

As a child, Jane's summers were spent with family at their cottage in Scituate. As Scituate held a special place in her heart, she returned in later life with her brothers Frank and Peter, and their families. On a recent trip to Scituate, Jane nostalgically recounted helping build the boat "The Mighty Mac" with her cousin, and watching its launch into the Scituate waterway. Social gatherings were often filled with Irish traditions, and of course, the appropriate adult beverage. She enjoyed cooking, including making the annual stuffed cabbage with family. Christmases spent with both the McCaffrey and McLaughlin clans were also a highlight. Over the years, Jane was also active in her community, serving as a Mariner Girl Scout, a member of the Parent Teacher Association, and a teammate on the roster of the Chelmsford Over 40 Soccer League. In a small kindness that grew into a beloved habit, Jane began mowing a friend's neighbor's lawn, and before long made a "business" mowing more than fifteen lawns for others.

In her final years, Jane received warm and compassionate care from the staff at Heights Crossing and Grace Life Care, for which her family remains deeply grateful.

Jane will be remembered for her vibrant spirit, her adventurous heart, and her enormous capacity for friendship and generosity. She gave her whole self to her students, her family and friends, and everyone lucky enough to know her, and her beautiful smile, warm laugh, and loving nature touched far more lives than she ever counted.