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The world lost a remarkable human being when Hugh Caldara, 73, of Stonington passed and sailed away to the Unknown Shore on Thursday, October 18, at Smilow Cancer Hospital in New Haven. He leaves behind the love of his life, his wife Joanne, and legions of friends. He was predeceased by his parents, Stuart and Betty Anne (Beebe) Caldara, of Stonington.

Hugh was happiest at the helm of any sailboat in a breeze. He sailed big and small boats around the world as an active member of the Cruising Club of America, the Storm Trysail Club, the N.Y. Yacht Club, and the Wadawanuck Club in Stonington. His extraordinary seamanship skills, good humor, and storytelling gifts made him the perfect shipmate.

Hugh’s biggest impact on the world, and his greatest professional gift, was as an educator. He was a legendary history teacher, varsity football and hockey coach, and athletic director for 41 years at The Gunnery School, in Washington, CT. Hugh inspired countless students to reach higher than they thought possible. He was inducted into the Gunnery School Athletic Hall of Fame, and was a past president of the New England Prep School Athletic Council Football Coaches’ Association, where an annual award was named in his honor.

Hugh grew up in Greenwich, CT, where he attended the Brunswick School. He graduated from the Taft School in 1964. After graduating from Coe College, Hugh served in the U.S. Navy, then completed a masters degree in history at Wesleyan University in Middletown, CT. He was also an avid and accomplished fly fisherman in salt and fresh waters.

A memorial service will be held in celebration of Hugh’s life at Calvary Church, 27 Church Street in Stonington, CT on 17 November, 2018, at 2:00 PM.

Donations in Hugh’s memory may be made to The Innocence Project, 40 Worth Street, Suite 701, New York, NY 10013.

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