50th annual world’s longest Sunfish race

late notice, but for those in the New York or east coast area, this weekend is the 50th anniversary of the world’s longest Sunfish race – a race around Shelter Island, NY.

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).

Southold Yacht Club – 165 N. Parish Drive, Southold, NY 11971

Saturday, July 10, 2021

To celebrate the 50th anniversary of this unique nautical marathon, Southold Yacht Club is pulling out all the stops. Sunfish singles and doubles fleets for both youth and adults will start together but be scored separately for awards purposes. Awards for first 10 finishers, adult doubles, youth doubles, and more! The title sponsor of the 50th Race is Laser Performance. They are donating one new Sunfish sailboat and two Sunfish racing sails which will be raffled off at the awards ceremony. Each sailors will get one free raffle ticket with registration. No additional raffle tickets will be sold. The odds are in your favor! Beach party and awards follow a beautiful day on the Bay!

photo via Southold Yacht Club

notice of race can be found here: NOR (.pdf file) and online registration is here at Regatta Network.

swag for/from the event can be bought online here.

Lee Montes has a “preparation” video he recently posted to get you ready for this race:

2 Responses to “50th annual world’s longest Sunfish race”


  1. 1 Clyde Osterhout July 9, 2021 at 8:35 am

    With the Hampton Roads race being in limbo, this might be my only choice for a Sunfish endurance race. 21 miles is a VERY long race! I think that I need to prepare for next year’s race by camp cruising down the sounds of The Eastern Shore. Cruising the sounds, camping on the dunes is rough (LOL) but no sacrifice is too great for victory (which in my case means actually finishing the race, and not finding myself lost off shore and heading for the Azores).

    Liked by 1 person


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