John “Jack” Carroll Howland Sr. passed away peacefully at home in Clearwater, Florida, at the age of 81, on February 29, 2024. He was surrounded and supported by many whom he loved, including John and Marcia Shaw, and Chris and Julie Regan.
He was born on August 11, 1942, in Boston, Massachusetts, the son of Robert and Margaret. He was predeceased by his brothers, Robert and Thomas. Jack married Joan (O’Neil) on September 4, 1964. Together, they had three children: daughter Carol, and sons Robert (with wife Gayle) and John. He was later married to Shirley, and became a stepfather to her two sons, Jason and Thad.
He was the proud grandfather of Riley, JJ, Bryce, and Joanie.
Jack served in the Navy in Air Antisubmarine Squadron Thirty-Four from 1961 to 1963. He was stationed at Guantanamo Bay, Cuba, during the Cuban Missile Crisis as part of the blockade.
In 1964, he became a Massachusetts State Trooper, graduating with the 46th Massachusetts State Police Training Troop. He was especially proud of this accomplishment and retired as a Lieutenant after 23 years of service. While in the State Police, he earned a Bachelor’s Degree from Worcester State College.
Jack had many friends and family with whom he enjoyed spending time. He especially loved living in Florida, playing golf, and cards.
A Celebration of Life will be held on Sunday, June 22, at Brimfield Winery from 12–4 p.m. He will be laid to rest alongside his wife Joan and daughter Carol in a private ceremony, surrounded by immediate family, at Westwood Cemetery.
Alfred Roy & Sons Funeral Home 12 Hammond St. Worcester is directing arrangements. To share a memory of Jack or to sign his guestbook, please visit www.Royfuneral.com