Brian Flanagan

Brian was born on January 8, 1953, the youngest of the late John and Irene (LaFarr) Flanagan. He grew up in Gardner, Massachusetts, and was a 1971 graduate of Gardner High School. He built a life with his family in Winchendon, a place he loved calling home. He was a devoted son, brother, husband, father, grandfather, uncle, and friend, roles he carried with love, loyalty, and pride. He loved his family fiercely, and they were always at the center of his life.

He spent his entire career in the grocery business, beginning as a butcher and working his way up to store manager at both Shaw’s and Price Chopper Supermarkets, before returning to his roots as a butcher, a role he cherished, prior to his retirement in 2016.

A lifelong fan of Notre Dame football and the Boston Celtics, he found joy in cheering on his teams and sharing those moments with the people he loved. He also took great pride in upholding family traditions—making Grammy Flanagan’s rolls, pepper relish, pickles, and fudge, and, never to be forgotten, faithfully carrying on the cherished Flanagan tradition of corned beef.

He was an avid gardener who loved sharing stories of each plant in his garden, taking particular pride in roses, peonies, and bleeding hearts, and often reminiscing about the tulips his father grew. Through his hobbies and everyday life, he imparted wisdom with simple, meaningful phrases, including: “Inch by inch, every job’s a cinch; yard by yard, you make it hard” and “If you’re failing to plan, you’re planning to fail”.

He was predeceased by his parents, his stepmother, Bertha Flanagan, three brothers, David, Kevin, and Daniel Flanagan, and his beloved wife of 43 years, Janet (Mattos) Flanagan. He is survived by his daughter, Kate Davieau, and her husband, Ben, of Ashburnham; his stepson, Anthony Delmonico, and his wife, Lynne, of Torrington, CT; and his stepdaughter, Ashlee Santerre, and her husband, Jeffrey, of Bedford; as well as five cherished grandchildren, Lucy, Charlotte, Logan, Jack, and Parker.

A funeral mass will be held at St. Denis Church in Ashburnham on Saturday, February 28, 2026, at 11:00 a.m.

In lieu of flowers, donations may be made in his memory to Mass General Brigham Hospital, Cancer Center, at https://giving.massgeneral.org/donate/mgb-cancer-institute.

To leave an online condolence, please visit www.mackfamilyfh.com

Stone Ladeau Funeral Home, 343 Central Street, Winchendon, MA, has been entrusted with his funeral arrangements