James R. Stewart, obituary
James R. Stewart passed away peacefully, at home surrounded by loved ones on Thursday, September 25, 2025.
Jay was the beloved husband to his wife of 54 years, his queen bee, Cheryl Evans Stewart, his three beautiful daughters—Alyssa Stewart Maddocks and her husband Peter Maddocks, Jessica Stewart, and Jennifer Stewart and the son he never had, Cecil Armstrong. He was proud papa to his three grandchildren: Gabrielle, Maddie and Brendan Coates.
He was predeceased by his father, James Stewart; mother, Claire Yvonne Stewart; and sister, Margaret Colantuno.
He was loved by so many especially beloved extended family: brother and sister in laws, cousins, nephews and nieces. And not to be forgotten his best friend since he was six years old, Jack Casey, where his favorite phrase “lie and deny” was most likely coined.
Born on July 31, 1946, in Salem, Massachusetts and raised in Swampscott, Massachusetts. Jay summered in Maine as a child at his grandparents' blueberry farm in Stockton Springs, Maine. He eventually put down roots in 1977, where he raised his family, and was a visionary creating our family owned and operated farm selling wild Maine blueberries roadside, the Maine way and on the honor system. Burning the fields was one of his favorite times, just ask the Stockton Volunteer fire department, they were here more than once for old Sparky. When they first moved here, they ran “Jay’s”— a local institution that may or may not have operated on good food and even better shenanigans. He worked at GE for years, starting in Lynn, Massachusetts and later transferring to GE OTH in Bangor.
Jay had many passions: playing cards (especially if he was winning), collecting antiques (mostly clocks that never had the right time); Jay and Cherie were the original American pickers traveling the country buying and selling antiques, that’s where he was dubbed “Jay from far away”. He was a proud veteran and provided unwavering support to the American Legion Hall, VFW Hall and other local watering holes – mostly for observation and supervisory purposes, of course.
He was a master of nicknames, a dog lover, so quick-witted, and a philosopher in his own right. He was also a staunch believer in marrying for money—but somehow ended up marrying for love, so go figure.
In his later years, Jay lived with Alzheimer’s, but thanks to his family’s care and devotion, he was able to stay comfortably at home—though that didn’t stop him from taking the lawn mower out for joy rides like it was a Harley. He loved hanging out at Jennifer’s food truck, JC’s On-A-Roll, sharing his love and wisdom with every passerby, especially if they had a child or a dog. Jay would often say, “If you want a friend, get a dog… If you want two friends, get two dogs.” His humor ranged from charming to “Dad, you can’t say that anymore.”
Jay was a friend to everyone—whether you wanted one or not. He had a way of leaving a lasting impression: loud, loving, and just the right amount of inappropriateness. His legacy, much like his jokes, will echo on for generations.
A celebration of his life will be held Saturday, October 11, from 1 - 4 p.m., at “The Farm” 416 Bangor Road, Stockton Springs, Maine. The family would love for all who want to come and share stories of Papa The Man, The Myth, The Legend, even if you only knew him as the blueberry baron or met him at one of his many hangouts, all are welcome.
Memories and condolences may be shared with the family at www.ripostafh.com