Shelter Island Duck Race is late summer crowd-pleaser
The Annual Duck Race sponsored by the Shelter Island Chamber of Commerce is an event that can be counted on for fun and, for a few winners, a lucrative payoff.
For weeks before the Aug. 24 race, the Chamber has been selling the chance to share in the proceeds if yours is the numbered duck to float across the finish line first. A few hundred numbers were sold, each corresponding to a rubber duck, all of which were scheduled to be dumped off First Bridge, where Chase Creek flows into Dering Harbor at “noon sharp” on Sunday.
As befits a maritime competition held on an island, the time of the outgoing tide necessitated a change in the event’s time to 1 p.m. Although that may have prevented a few participants from attending, there were still plenty of eager competitors and cheerful fans to watch the hard-fought race.

Maddie Chulsky, age 9, and her “really good friend” Annika Philipp, who turns 10 this week, were there along with Annika’s brother Connor, 6. They were urging folks to buy a duck right up until race time. Asked if they were trying to support the Chamber, Maddie explained that they had bought their ducks, and had calculated that the more people who bought ducks, the larger the pot would be for the winner to share. The girls said they were finishing up a happy summer of day camp at Camp Quinipet and the win would really top off their season on the Island, where, Annika said, they come “every single year.”
Alas, they’d have to be content with a summer of memories, as the prizes went to Janine Derby, Isabelle Topliff and Sam Radovic, who took home 10%, 5% and 2.5% of the proceeds, respectively.
The event was not without a ripple, although the winning duck, as almost always happens, was the one that sat in the lead position from the moment they hit the water.
The effect of the wind and tide, however, had pushed the rearmost ducks to the west, where some of them became wedged between the bridge foundation and the eelgrass by the shore. Emcee Ken Lewis Jr., impossible to ignore in his own giant duck costume, dispatched one of the judges in a kayak to nudge the stragglers free with his paddle. He complied, even picking up a few ducks and tossing them into the harbor to overcome their handicap.
The unfolding drama captivated a family who had been staying in Southold and heard about the event, so came to explore the Island. Ayla Rahman, 6, sister Clea, 4, and their parents Erin and Irfan were treated to a tour of the Shelter Island Police boat that’s stationed at the dock below Volunteer Park by Constable Beau Payne.
Once the event was over, the visitors strolled Bridge Street and ducked into a few of the shops to see what else Shelter Island had to offer.

