By Beth Fleisher and Celeste Flick, Regatta Co-Chairs


Five-time winner John Eckart is looking for his sixth victory this year.   Photo courtesy of Southold YC


Southold Yacht Club in Southold, NY is hosting the 50th Annual World’s Longest Sunfish Race Around Shelter Island, NY on Saturday, July 10, 2021. This unique nautical marathon is open to single and doubles Sunfish sailors per the event NOR.

As the crow flies, the nautical distance around Shelter Island, starting and finishing at Southold Yacht Club, is 21.3 miles. Since crows don’t tack, however, it is estimated that the distance for the average race sailed over the years is the equivalent of a nautical marathon (approximately 26 miles).

The World’s Longest Sunfish Race has become one of the most exciting, enduring and popular competitions on the Sunfish Class calendar. Sunfish sailors from across the country have enjoyed spirited competition in sometimes challenging conditions that vary wildly from year to year.

Yearly participation has ranged from 35 to 55 Sunfish sailors ages 16 to 92. The youngest winners were Mary Beth O’Brien (Southold Yacht Club, 1977) and Shane Sullivan (Southold YC, 1988) at age 17. The oldest winner is Dick Heinl (Seawanhaka Place Yacht Squadron, 2011) at age 86. Heinl also holds the record as the event’s oldest participant (2017) at age 92.


Sunfish racers pass Bug Light in Gardiners Bay.   Photo courtesy of Southold YC


The average winning time is 4:51; the 4-hour mark has been broken nine times. The course record is 3:23 set by Todd Klinger (Narrasketuck YC) in 1999. John Condon (Southold YC) and John Eckart (Massapoag YC) have each won the race five times. Both are sailing for a sixth victory in 2021.

Many participants return to Southold to race every year. Joe Sullivan (Southold YC) holds the participation record of 47 races. Joe is one of the founding fathers of the race and, at age 84, plans to extend the record in 2021.

Race registration includes entry to the race, t-shirt, continental breakfast, drinks and a lively post-race awards ceremony and party. Awards will be presented to the top ten Sunfish singles finishers, first place doubles, first youth single, and first youth doubles. (Additional awards may be awarded for doubles and youth dependent on participation.) Perpetual awards (maintained at Southold YC) are presented to the winner of the race, the first female finisher and the oldest participant and first master finisher. All competitors will receive a personalized Certificate of Completion.

Registration opens April 1, 2021. For information and to register, please go to ■

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