Randolph Bailey

Northborough, MA – Randolph Bailey, aged 89, died on January 9, 2026, at 8:44 p.m. at the Coleman House. He was surrounded by many loved ones until his passing. He previously lived in Sterling, MA, and most recently at the Highlands in Westborough and Whitney Place/Beaumont in Northborough, MA. Randy was born in Boston, Massachusetts on September 30, 1936, to Rebecca Bailey. His wife Geraldine Anne Bailey predeceased him on January 6th, 2018.

Randy is survived by his 4 children, 9 grandchildren and two great grandchildren: his daughter, Andrea Bailey and her husband Ray Bazzano, Ed Bailey and his wife Marlene, Ray Bailey and Phil Bailey. He leaves his grandchildren: Amanda, Kari, Tyler, Caitlin, Samantha, Rebecca, Annie, Alex and Krystal. He is also survived by his brother, John Bullard, and his wife, Anna, of Maine; his cousin, Barry Caminati, and his wife, Jackie, in Vero Beach, Florida; extended family residing in New Hampshire; as well as numerous friends across Massachusetts, California, and Florida.

Randy was an honorable member of the military serving in the Navy from 1958-1962 as a Radio Communications Operator. He loved being with his family and friends and was known for his wonderful sense of humor. He loved to travel the country with his wife and lived in an RV for over 10 years. He was an enthusiastic Red sox and Patriot fan, playing many sports with his children when they were younger and recently bean bag baseball with his friends. He enjoyed long walks, playing pool and bingo, relaxing at the beach, spending time with family, boating, swimming, and fishing, as well as savoring Dunkin coffee and jelly donuts.

Randy adored and loved his children, grandchildren and great grandchildren with unconditional love. Always with a smile, he had a gentle, kind, and loving heart, and will be greatly missed by his family and friends. He will be forever in our hearts.

Dad, Grandpa, Gigi. Miss you. Love you.

The interment and burial service for family members will take place on Thursday, January 22, 2026, at the Massachusetts National Cemetery, Connery Avenue, Bourne, MA. In lieu of flowers, please donate to your local Veterans Association or the Alzheimer Foundation.