Stephen Leonard Obituary
A Life Full of Laughter, Love, and Adventure
Stephen Mark Leonard, 75, of South Burlington, passed away on November 5, 2025, of natural causes at his home, leaving behind a lifetime of stories, laughter and memories that will be shared for years to come.
Steve graduated from South Burlington High School in 1968 and went on to graduate from the University of Vermont in 1972, where he played one season of fall soccer, a sport for which he remained passionate his entire life. He also found joy playing tennis and attending The US Open in New York City each year. He spent a major part of his adult life in Boston where he established roots in a community of lifelong connections. He was a true Boston sports fan, especially of the Red Sox and Patriots.
Steve was a devout Catholic, attending weekly Mass. He trusted in and followed his Lord, which was evident in his kindness to and interactions with everyone.
His family was paramount to him. He loved spending time with them - holidays, game days or just hanging out and catching up. Those were his happiest times.
Steve was a deep thinker and avid student of life, always ready with insightful and humorous quips. He lived life on his own terms. He was an exceptionally bright, adventurous, well-traveled free spirit, often using his fluency in Spanish throughout his travels. He never passed up a chance for a new adventure - whether backpacking across South America, exploring Europe, or enjoying adventures closer to home in the US.
Music played an important part in his life as there was always a song playing in the background. At the age of 19, he even attended the Woodstock Music Festival, a testament to his free spirit and love of experiencing life to the fullest.
He will be remembered for his humor, his warmth and his gift for finding joy in the everyday. His quick wit, big heart and infectious smile made life brighter for everyone lucky enough to have known him.
Stevie was surely his mother's "red-headed pepper pot".
Stephen will be sorely missed by all and live on in our hearts. He is survived by six loving siblings:
Daniel Boles Leonard and wife Linda of Ryegate, VT, Michael Dean Leonard and wife Patricia of Austin, TX, Kathleen Leonard Gordon and husband Robert of Burlington, VT, Thomas John Leonard of Starksboro, VT, MaryBeth Stark of Minneapolis, MN and Peter James Leonard of Shelburne, VT
He also leaves behind many nieces and nephews who were dear to his heart. Stephen was predeceased by his parents, Dean and Edie Leonard of South Burlington.
A Mass of Christian Burial will be celebrated on Saturday, November 15, 2025, at 10 am at St, John Vianney Church, 160 Hinesburg Road, South Burlington. A private family burial will be held at a future date.
Arrangements are in the care of the Chittenden County Cremation Society, a division of the Ready Funeral and Cremation Services. To send online condolences please visit www.cremationsocietycc.com.
To send flowers to the family or plant a tree in memory of Stephen Leonard, please visit our floral store.
To plant trees in memory, please visit the Sympathy Store.
6 Entries
Alan Hunton
November 14, 2025
I was lucky enough to be Stephen's closest friend and nearly constant companion for the last 70 years. My mother used to proclaim, "if Stevie Leonard jumped off the Winooski bridge, you'd be right behind him". We were classmates at Central School, SBHS and UVM and fellow brothers at Sigma Phi Epsilon fraternity. Voted the "class clown" at graduation in 1968, that captured how he touched everyone with his intelligence and razor wit. We shared so many "private jokes" throughout the years, I couldn't count them. Steve was an excellent athlete, and despite his short stature, he made up for it with hustle and determination. He was the starting QB on the football team and a starter on the basketball and baseball teams. He made the freshman soccer team at UVM (with me) having never played it in high school. Later in life, he took to tennis and became a "tough out" on the courts in Boston and Burlington with his speed and racket skills. Steve loved all kinds of music, especially Bob Dylan and Van Morrison, and he had amassed considerable libraries of vinyl and CDs. We shared a quirky habit of "speaking in lyrics", borrowed from some song we knew when appropriate. Steve traveled extensively from Central and South America to Ireland and the UK, Spain, France and Italy. Steve was a devout Catholic and attended mass wherever he found himself. His faith was unfortunately tested by the loss of two of his girlfriends, one in the Lockerbie terrorist bombing and another later by suicide. Steve was lucky enough to be one of the "Leonard clan" of South Burlington. Dean and Edie had seven children and every one of them made a positive mark in our community. Steve loved each and every sibling and enjoyed spending time with them. They were and still are my "second family" and treated me as one of their own since I was always with Steve. Needless to say, he will be sorely missed by those of us lucky enough to have known him. RIP to my brother from another mother. See you in heaven.
Bradley and Lynn Gordon
November 13, 2025
Stevie was as nice a person as we have ever had the privilege of knowing. Despite more than his fair share of heartache, his spirit and his kindness touched all who knew him. His smile warmed everyone.
Dave Burrell
November 11, 2025
Such a great man and friend - thanks for all the great memories....
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JoAnne Bowery
November 11, 2025
You were definitely one of a kind in this world, lived the life you wanted and by your own rules. I find it hard to believe you are gone and will keep all of our memories in my mind. Rest in peace my friend. JoAnne
Leonard Olds
November 10, 2025
Steve you were always a fun guy to work with. I wish there was more time. RIP <3 Lenny
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