Jonathan 'Jack' 'Jack' Gaylord

STERLING - Jonathan “Jack” Gaylord, 79, a lifelong resident of Sterling, passed away on Monday, September 8, 2014 at River Terrace in Lancaster after battling a rare debilitating neurological disease (Shy Drager Syndrome).

Born in South Boston in 1935, he was the son of the late Olga E. (Mitchell) Gaylord and well known vocalist, Chester Watson Gaylord. He is survived by his beloved companion, Barbara Marble of Champaign, Illinois; cousins, Ann Mitchell Waters of Cape Cod and Paul R. Mitchell of Paxton. He is also survived by his former wife, Karen H. (Lind) Gaylord of Sterling; and dear friends, Mary Nourse, Roy Dohlstrom and Curtis Lanciani.

Jack was the quintessential “townie”...he would race home after school, grab a fishing pole and fish until supper time. In the winter he would get up at 4:30am and run outside to ride on the plow truck. He attended elementary through 9th grade in Sterling. He graduated from Cushing Academy, Ashburnham in 1954, where he excelled at soccer (MVP) and track.

He joined the United States Marine Corp in 1954. He was assigned to Admiral Jerauld Wright, Commander-In-Chief of The U.S. Atlantic Fleet as a Flag Orderly stationed in Portsmouth, VA. He would often say “not bad duty for a young guy from Sterling”. After returning to New England, he attended Northeastern University in Boston before joining the Massachusetts State Police. As a state trooper he was one of the first undercover narcotic agents (1971), commonly referred to as “The Hippie Cop”. Jack firmly believed that his service to his country as a Marine and to the Commonwealth as a trooper were the two proudest decisions of his life.

He retired from the State Police in 1985 and spent his retirement at Hardscrabble Farm in Sterling breeding Yorkshire, Hampshire and Landrace pigs. He was passionate about his livestock dogs, often having as many as five Australian Blue Heelers.

In the late 1990s and well into 2000, he and Barbara traveled to Iles de la Madeleine, QC, Lauderdale By The Sea, FL, and twice cruised on The Mississippi River aboard the historic American Queen paddleboat. Jack was an avid bird watcher and especially enjoyed Sunday morning flea markets. For many years during the holidays he volunteered at The Bishops Table in Worcester serving food to those in need. He would joke that he finally made it up the serving line to from rolls to dark meat, his favorite. Everyone understood and admired his amazing sense of humor. He will be remembered as a ‘guy’s guy‘and will be missed by an enormous cadre of friends, particularly those with whom he held court daily at The Over Easy Cafe. He was simply the salt of the earth.

Relatives and friends are invited to attend calling hours on Saturday, Sept. 13, from 9 to 11 a.m. followed by service at 11 a.m. in the Miles-Sterling Funeral and Tribute Center, 100 Worcester Road, Sterling. Burial with full military honors will follow at Oak Hill Cemetery in Sterling. Donations in Jack’s memory may be made to Vanderbilt Multiple System Atrophy Gift Fund, c/o Vanderbilt University Gift Processing-PMB 407727, Nashville, TN 37240-7727. Please make checks payable to Vanderbilt Medical Center. If you wish to pay respects please use our "guest book" on this page.