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Cindy A. Chesmore

April 23, 1949 - April 9, 2018

Visitation: Friday, April 13th 4:00-8:00 p.m. Chesmore Funeral Home of Hopkinton

Funeral Mass: Saturday, April 14th 10:30 a.m. St. John the Evangelist Church, Hopkinton. (Please meet directly at church)

Burial to follow at Mt. Auburn Cemetery, Hopkinton



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Cynthia Ann Chesmore, 68, of Hopkinton, passed away Monday, April 9, 2018 at the Metrowest Medical Center in Framingham, as a result of COPD. Born in New Haven, CT, she was the daughter of the late Helen (Rafferty) and Armand P. Castiglioni. She was the wife of 48 years to Robert L. Chesmore of Hopkinton.

Cindy was raised in Connecticut and was a graduate of Laurelton Hall in Milford, CT and Graham College in Boston; where she met her husband, Bob. Prior to starting her family, she worked at John Hancock Insurance, State Street Bank, and Damon Labs. She was instrumental in helping Bob run both of the family’s funeral homes for many years. For over 30 years, she has been the Director of the Hopkinton Senior Center, a career she has truly loved. She spearheaded the facilitation for a new senior center for many years. She was extremely proud of the growth and achievements of the center; especially when it went from being in the basement of the Town Hall to the large, beautiful center it is today. Cindy was well-liked and took pleasure in spending time with her seniors and meeting new people. She was the founder of the annual Veterans’ Appreciation Dinner and Veterans’ Breakfast at the Center.

Cindy was a co-founder of the Polyarts Committee; a member of the Hopkinton Historical Society, Long Pond Association in Maine and past member of the Women’s Club in Hopkinton.  She was the treasurer of Ye Olde Village Corp and the past VP and treasurer of Thayer’s Trucking Co. She enjoyed her time as a CCD teacher while her children were young. In her better days, Cindy enjoyed traveling the world with friends, and her yearly visits to Altamira in Jamestown, RI. She especially enjoyed spending her free time during Spring through Fall, at her and Bob’s camp in Maine.

Besides her husband, she is survived by her son, Keefe M. Chesmore and his wife Andrea; her daughter, Aimee B. Rizzo, and her three beloved grandchildren, Cassie Rizzo, and Gregory and Andrew Chesmore, all of Hopkinton; and her dog, Addie. She was predeceased by her sister, Linda Kolon.

Visitation will be held on Friday, April 13th from 4:00-8:00 p.m. at the Chesmore Funeral Home of Hopkinton, 57 Hayden Rowe St. www.ChesmoreFuneralHome.com A funeral mass will be celebrated on Saturday, April 14th at 10:30 a.m. at St. John the Evangelist Church in Hopkinton. Please meet directly at church. Burial will follow in Mt. Auburn Cemetery in Hopkinton. In lieu of flowers, donations may be made to Friends of the Hopkinton Senior Citizens, 28 Mayhew St. Hopkinton, MA 01748.