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 about which he remained passionate his entire life. He also found joy playing tennis and attending the U.S. 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 U.S.
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 “redheaded 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, Texas; Kathleen Leonard Gordon and husband Robert of Burlington, Vt.; Thomas John Leonard of Starksboro, Vt.; MaryBeth Stark of Minneapolis, Minn.; 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, 10 a.m., at St. John Vianney Church, 160 Hinesburg Rd., South Burlington, VT. 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 Ready Funeral & Cremation Services. To send online condolences, please visit cremationsocietycc.com.
This article appears in The Winter Preview Issue 2025.
My deepest condolences to the family. I enjoyed his humor and friendship over the years. May he rest in peace.
I’d encounter Stephen many times when walking the halls of the building where we both resided. I’d day “how ya doin,” he’d always reply: “mediocre.”
I found that to be funny… I was shocked to hear of his passing, as I’d chatted with him just a couple of days prior. A wave of neighbors have passed in the last few weeks, leading me to reflect on just how tenuous our grip on life is.
I look at his door as I walk by, his Red Sox logo is gone, as is he.
Do something nice for someone in Stephen’s memory–he’d like that.
I had the privilege of being one of Stephen’s housemates during the mid-90’s, a time that now seems even more treasured and idyllic than it was when I was living it. Stephen became for me a brotherly figure, a trusted rock solid friend and confidant as we shared our bohemian existence on 262 Cabot St. after I was married I always kept contact with him, even texted with him the 2 days prior to his passing, and had plans for a visit to S Burlington to take him out for dinner and a UVM basketball game. my wife and I are deeply saddened to have lost such a unique and charismatic friend. had to walk outside yesterday looking up at the trees and the leaves on the ground and played some classic early Dylan in Stephen’s honor as I wiped away the tears. gone too soon, gone but not forgotten, and one of a kind. miss you already Stephen.
I was very sorry to rad of Steve’s recent passing. I worked with Steve at Avis and at Vital Delivery Green Mountain Messenger we had many longer conversations in are rides. Steve was a very good friend.
I am Lita Knickerbocker and Steven Leonard was being my best friend. He would do me a favor and I would do a favor for him too. I always make extra food for him cause he doesn’t cook then he go shopping at the food shelves and he will share me some of The food he would accompany me go fishing and do a little smoking pot from day one he moved into the PINES. We became good friends. He had given me rides when I needed him . Steven is so smart intelligent and he always stop by my apartment in 217 and both of us will watch Jeopardy and he could answer most of the answers questions. most of my Filipino friends know him very well and really like him. He always join us in our crowd fiesta. I was really sad and sad when I learned he passed away. Steven I miss you as my good friend.
My deepest condolences to the Leonard family on Steves passing. Steve was a good friend and part of the tennis group that meet on Fridays in Dedham Rackettime and the afters!! He was always full of fun and mischief! Steve also travelled to Ireland for our wedding and dived right in with friends and family there. I have many fond memories of Steve and will buy a pint of Guinness in his honour. Ar dheis dè go taibh a anam.