DEAL ISLAND, MD - History repeated itself today on Deal Island as crowds gathered to watch the 65th annual Skipjack Races. These historic vessels, once the backbone of the Chesapeake Bay's oyster dredging industry, are now the last working boats under sail in the United States.

In their prime, fleets of skipjacks dredged oysters from the bay's floor, but today, the wind in their sails plays a big role in these races. This year's windy conditions brought both advantages and disadvantages.

The day began with the blessing of the fleet for the nine skipjacks competing, followed by the national anthem. However, the wind delayed the start by an hour. Eventually, the boats made their way to the start line by 10:30 a.m., either under their own power or in tow.

The annual event attracted its usual crowd of spectators. “We love the Skipjack Races. We try to come down every year. Usually, we’re out on our own boat, just kind of watching from out there. We’ve had some rides on some skipjacks—we have some friends that own them,” said Dede Singleton, an annual attendee.

Jennifer Jones, another spectator, shared her enthusiasm: “It’s a unique experience to the Eastern Shore. You come to Deal Island, cross over the bridge, and you’re experiencing something you can’t experience anywhere else.”

Mike Singleton echoed the sentiment, emphasizing the importance of preserving this tradition. “You know, this is part of what went on. It’s a part of the Chesapeake Bay—how they used to make a living with these boats. Now that there’s not many around, we need to show the respect that we need.”

Despite the excitement, about an hour into the race, several skipjacks began dropping their sails and calling it a day, including the Ida May, a vessel built in 1906.

“The Ida May is a really light boat, and it was pretty breezy, so we put in as many reefs as the boat could handle. But it wound up being too much for the boat, so we decided to do the prudent thing and drop sails. We’ll live to sail another day,” said Captain Shawn Ridgley of the Ida May.

However, the windy weather worked in favor of this year’s winner, the H.M. Krentz, a skipjack built in 1955.

“When it’s light air, my boat’s built heavier and has a shorter rig and doesn’t drive as well. But in conditions like today, she performs really well, and I was very pleased to get a good start,” said Captain Ed Farley of the H.M. Krentz.

The H.M. Krentz was one of the two boats still competing as it crossed the finish line. Despite some minor damage caused by the wind for some skipjacks, all boats returned safely.