Bernard "Bernie" Caliendo

Bernard "Bernie" Caliendo, 71, of Windsor, passed away peacefully on Tuesday, September 16, 2025.
Bernie was born in Hartford, son of the late Camille (Stephenson) Caliendo, attended AI Prince Technical School, and graduated from Windsor High School. He was a talented athlete and competed in track, hockey, and football, and played pony football for the Vikings, where he was their team captain for two years. As a young man, he was fortunate enough to discover two passions that he excelled at, music and carpentry. His neighbor, who was a master carpenter, took him under his wing and taught him his trade, a career that would take him through his older years. Music was always a big part of his life and in elementary school, his friend, Mark Lepak's dad, renowned musician, Alexander Lepak, taught him how to be a drummer. Bernie participated as a drummer in the St. Gabriel's Fife & Drum Corp and in a band with his high school friends. Shortly after high school, Bernie embarked on the journey of a lifetime when he accepted a job with DD Smith & Company and traveled around the world as their sound and lighting technician. His proudest and most exciting moments of that career was when DD invited him on stage to sing with him. Bernie also spent some time in the early 80s touring with Mr. Big around the Connecticut area. During that time, he started his second career as a self-employed carpenter, working on home renovations, building furniture and cabinets, and general woodworking and electrical. For over 20 years, he served the Windsor and surrounding communities until he segued into his own home inspection business, "B Sure Home Inspection," which he owned and operated for the next 20 years. Bernie was an integral part of the Windsor community and was the first chairperson of the Home Inspectors Licensing Board, the president of the CT Association of Home Inspectors, and a member of the Exchange Club, the Historical Society, and the Lion's club. Bernie was also a communicant of St. Damien of Molokai, St. Gabriel Church in Windsor. His strong work ethic and drive inspired his family and friends to be the best they could be every day.
Bernie was an amazing father, brother, uncle, and friend who put his family above all else. He taught his children the value of family, hard work, loyalty, respect, discipline, and how to treat others the way you would want to be treated. Bernie loved his kids dearly, attended all their events, and supported their dreams. It would be hard to find a man with a bigger heart, and he would give you the shirt off his back or the last dollar in his pocket if you needed it. Everyone knew him for his big smile and his willingness to talk to anyone. Bernie will be remembered as a sweet, sentimental, and nostalgic man who showed his love to many different people in many different ways. He enjoyed doing things his own way, but he had a heart of gold, and everything came from a place of love.
Bernie was often the life of the party and loved being in the middle of a celebration. He had a great and playful sense of humor and loved to play friendly pranks on his family and friends. He enjoyed cooking traditional American and Italian dishes and looked forward to participating in family chili cook-offs and always followed his rule of "the hotter the better." Bernie kept his love for drumming alive and well in his life and especially loved listening to the Beatles, NRBQ, and the Young Rascals. He was passionate about his politics and enjoyed watching the news and giving voice to his opinions. His softer side enjoyed writing poetry, drawing, and reading historical books. Bernie also loved golf, fishing, photography, skiing, and watching gangster movies.
Bernie leaves a legacy of beautiful memories that will live in the hearts of those who knew and loved him.
Bernie is survived by his children, Alexander Caliendo of Windsor Locks and Camille Caliendo of Portland, ME; their mother and his former spouse, Diana Caliendo of Suffield; his siblings, Stephen Caliendo and his wife Karen of East Windsor, Fran Shea of Bristol, Rita Tryon of Canton, and Carol Toce and her husband Mark of Windsor Locks; his nephews, Chris Toce and his wife Megan and Andrew Toce and his wife Kaytlynn Wiecek; as well as other relatives and many friends.
His family will receive friends on Friday, September 26, 10-11:30 a.m., at Carmon Funeral Home, 807 Bloomfield Ave.,, Windsor, followed by a procession to St. Damien of Molokai Parish, St. Gabriel Church, 379 Broad St., Windsor, for a Mass of Christian Burial, 12 Noon.
Burial will be private in St. Joseph Cemetery, Windsor.