| Television news coverage from Deal Island's 67th Annual Skipjack Race, featuring the historic Chesapeake skipjacks, the Labor Day tradition, and the continuing effort to preserve and promote skipjack racing.
Deal Island Hosts Annual Skipjack Race
September 7, 2026 Braden Hamelin
Watch the video............................https://www.wmdt.com/2026/09/deal-island-hosts-annual-skipjack-race/
Deal Island, Md. — Skipjack racers hit the water early Monday morning, kicking off the 67th annual Deal Island Skipjack Race. The event is a storied part of Deal Island culture and drew a slew of spectators watching the race and checking out the various vendors in attendance.
People come for a variety of reasons. Some like to check out the activities and catch a glimpse of the boats, while others are locked in with a personal stake in the outcome.
“I actually know one of the skipjack captains, Captain Stoney. We’re trying to find his boat now. That’s the fun of it always, you really don’t know where anybody is,” said Michael Webber, who was spectating Monday’s race.
Another family had their father’s truck engine powering one of the boats.
The event also featured plenty of activities for the kids and families. Volunteer Matthew Kerm said Deal Island doesn’t always have a high volume of events throughout the year, making it nice to provide something local for the kids to enjoy.
“We don’t have a lot of local activities, so it’s nice that we can be in the hometown for some of the kids from the area or even the outlying areas. There’s not a lot like this. Labor Day is our big event,” Kerm said.
Attendees were feeling that family-friendly atmosphere, like local parent Taylor Pietrowsky. Pietrowsky and her kids were attending the event for the second year running and she said she hopes the event becomes a family tradition.
“I just enjoy the family feel that is here and Deal Island. I moved down here last year, and it’s just very welcoming,” Pietrowsky said.
The event connects generations across the area, according to Glenn Webster, the director of the Skipjack Historical Society.
“You’ll see three generations of people here and there, from grandmoms, grandfathers and sons and their children,” Webster said. He added the competitive fire of the racers is something that makes the annual tradition special.
“Once you get the first saltwater hitting your face, you’re done. You got be in the water. It’s what makes you a waterman to be competitive. That’s why they race. They started to race because of the competitiveness. Because everybody says, ‘I can beat you or you beat me.’ Go race for it,” Webster said.
The skipjack race organizers are looking to turn the Deal Island annual event into a Triple Crown competition, similar to the famous horse races. There are two more races planned around the area in the coming weeks, with Stoney Point hosting on Sept. 13 and Cambridge on Sept. 26.
Categories: Local News, Maryland, Top Stories
Tags: 67th annual skipjack race, boat docking, boat docking competition, boating, deal island, Skipjack race, somerset county |
