Dwight Jennings

Dwight Jennings, 58
1966 - 2025
Marblehead, MA - Dwight David Jennings, 1966 – 2025
Sailor, Brother and Devoted Friend
It is with a heavy heart we share that Dwight passed away two days shy of his 59th birthday.
Dwight Jennings was born and raised in New Canaan, CT. The only son to Alice and David Jennings, he gracefully navigated being the middle child to two older sisters and two younger sisters. He spent many summers in Maine at Camp Agawam and attended Trinity Pauling in New York. He received his bachelor's degree from the University of Tampa.
He was passionate about learning everything about a subject that interested him – his latest subject being Crypto and related companies in that industry. He could give gardening advice with great insight – a hobby that he learned at the hand of his maternal grandfather, Edwin Eberman. He was a dedicated history buff and the best to watch a sports event with – citing stats and side stories. He was an avid reader and writer and was working on a fictitious novel inspired by the Newport-Bermuda race in the 1940s. Most recently, he became a self-taught wood carver, carving whales that he enjoyed gifting to friends and family. To many he was a long-time friend and his loyalty in those friendships withstood the test of time.
Upon moving to Marblehead, MA in the early 1990's Dwight went sailing and was hooked. Over the next 30 years, he sailed competitively on many boats out of Marblehead harbor, sailing several years in the Newport-Bermuda race, Halifax, America's Cup Jubilee and Figawi.
He is predeceased by his father David Jennings. He is survived by his mother and stepfather Alice & Eric Dalrymple, Naples, FL. He is also survived by his sisters Janet Smith (Tim), Ipswich, MA, Gail Jenkins (Chris), Lookout Mountain, TN, Amy Duke (David), Atlanta, GA and Linda Kitzman (Mike), Lookout Mountain, TN. and nieces Claire Rehm, Kylie Lee, Lindsey Thomas, Sophie Duke and Lucy Kitzman.
His inner peace was sailing, and he always signed off any conversation or text with "Safe Harbor" – a term wishing a secure place.
In keeping with Dwight's wishes, his immediate family will hold a private ceremony to honor his life.
Because Marblehead and the sailing community deeply influenced Dwight's love of sailing, we invite those wishing to honor his memory to consider a gift to this foundation that supports sailing for children in underserved communities:
Corinthian Sailing Foundation
PO Box 4011
Nahant Street, Marblehead, MA 09145
Service Information: In keeping with Dwight's wishes, his immediate family will hold a private ceremony to honor his life.