Stephen Anthony Sylvestro

Although cancer won on Sept. 6 after a 15-year battle, Stephen Anthony Sylvestro rarely lost a race. An elite athlete since the ’70s, he regularly placed in the top 10 in his age group in the many road races, triathlons, biathlons, and adventure races in which he competed. These, along with his shock of white hair, warmth, humor, and many contributions to town life, made him, along with his wife, Debby, a fixture in the Fairfield community.

Born in 1950 in Worcester, Mass. to Anthony Paul Sylvestro and Jeanne Marie Taylor, he attended the Thorndyke Road School and Assumption Prep where he excelled in football and baseball. Later, at Trinity College in Hartford, he rowed crew. In 1973, he married his high school sweetheart, Deborah Miller, and would have celebrated their 47th wedding anniversary on Sept. 15.

He began his lifelong career working with children with learning disabilities as a teacher and coach at Eagle Hill School in Hardwick, Mass. In 1981, he helped found Eagle Hill-Lloyd Harbor in Long Island where he was assistant headmaster. In 1985, he and his family moved to Fairfield, Conn. to help open Eagle Hill-Southport, now The Southport School (TSS). There, he was dean of students and athletic director for many years, then dean of admissions until his retirement in 2015.

When not in racing shorts and jersey, Steve was most comfortable in a blue blazer, oxford shirt, khakis and tie as he guided students or acted as auctioneer for benefits for Fairfield Theater Company (FTC) and TSS.

With his sons Trevor, marketing director at FTC, and singer/songwriter Christopher Robin, Steve was active in the music and arts scene. That expanded when his granddaughter, Ava, began performing at Unquowa School and Broadway Method Acting. He was energized and fortified further by the birth of his effervescent baby grand-daughter, Taylor Poppy.

In recent years, The Mission, a health and wellness center for cancer survivors supported by the Connecticut Challenge, was a source of strength, solace, well-being, and enduring friendships for Steve and Debby.

Steve’s diagnosis in 2005 gave his family and friends 15 years not knowing how long they had with him, so opportunities to be together were treasured. His life was lived fully, with travel, annual reunions on Block Island, guitars and gatherings at Old Post Tavern, and plenty of ice cream trips with his granddaughters. Steve will forever be held in the hearts of his wife, Debby, sons Christopher and Trevor, daughter-in-law Lisa, brother David Paul Sylvestro and his wife, Lea, granddaughters Ava and Taylor Poppy, Debby’s sisters and in-laws, and Steve’s nieces and nephews as well as his many friends.

A private family service will be held. In lieu of flowers, donations can be sent to the Fairfield Theatre Company and The Southport School.

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