Raymond Stackpole

April 3, 1941 – December 13, 2024

Raymond Smith Stackpole passed away peacefully surrounded by family at his home on December 13, 2024, at the age of 83, after a long battle with cancer. Born on April 3, 1941, at Leonard Morse Hospital, he was the son of the late Phyllis Strange Stackpole and Earl Smith Stackpole.

Ray grew up in Natick and graduated from Natick High School in June 1959. He enlisted in the National Guard Reserves in September 1959. He was a self-employed finish carpenter his entire life. He learned the trade from his maternal uncle, the late Bud Strange. He was an avid reader of non-fiction. He also enjoyed fishing and was a devoted fan of NASCAR. Ray was considered a “Jack of All Trades” – versatile in skills of auto repair, plumbing, electrical work, and all varieties of small appliance repair.

Ray is survived by his wife, of 44 years, Eleanor Woodworth Stackpole, his daughter Lori Anne Whynot, and her husband Neil of Waltham, MA, his son Daniel Earl Whynot of Worcester, MA, and his son Jeffrey Earl Stackpole, and his wife Alicia of Medway, MA. He leaves behind two brothers – Howard Stackpole and his significant other Shirley Connolly of Norton, MA, and his brother Leonard Stackpole and his wife Karen of Holliston; his granddaughters, Hailey Perry and her husband Ryan of Norton, Alivia Jean Stackpole of Medway and his grandson Logan William Stackpole of Medway. Ray is also survived by several nieces and nephews – Cheryl MacInnis Jackins and her husband Andy of VT, Darlene MacInnis Sweet of NH, Catherine Stackpole of NY, Wayne Stackpole and his wife Danielle of Sudbury, and Johnny Stackpole of Billerica, and by his grandnieces Natalie Cullen of VT, Gabrielle Dante of Florida, and grandnephew Grant Cullen of VT, and a Great Grand Nephew Everett of Florida. Ray also leaves behind many cousins. He is predeceased by his mother Phyllis Strange Stackpole, his father Earl Smith Stackpole, and his sister Nancy Stackpole MacInnis.

Visitation and Memorial will be held at Chesmore Funeral Home, 854 Washington St., Holliston, on Monday, December 23rd from 12:00 Noon – 2:00 PM followed by burial and graveside service at St. Mary’s Cemetery in Holliston. In lieu of flowers, donations in his memory can be made to the Visiting Nurse Care Network – Fund Development (VNA) Milford Hospice. Address: 100 Trade Center Suite G-500, Woburn, Ma. 0180. Our sincere appreciation to his devoted nurses and caregivers – Sue, Katie, Marian, Youbide, Krysia, Doreen, Lauren, and Regina.