For the first time in decades, the majority of the Chesapeake Bay’s surviving historic skipjacks will be in Maryland’s capital, racing and sharing their stories with the public. The first ever Skipjack Heritage Days, happening at Sandy Point State Park alongside the Maryland Seafood Festival Sept. 13-14, revives a tradition that has been extinct for 35 years.
The popular Chesapeake Appreciation Days , held from 1965 to 1990, wowed visitors with skipjack races and oyster shucking contests. A 1990 Baltimore Sun article touted the event’s jousting tournament, pig races, and helicopter rides. Even in 1990, the Sun noted that the skipjack fleet had “sadly dwindled”. Chesapeake Appreciation Days was discontinued after that.
Now in 2025, fewer than 20 of the 1,400 skipjacks that once sailed the Bay remain in working condition. That makes it particularly important to keep the enthusiasm going for these wooden single-masted, shallow-draft workboats.
On Maryland’s lower Eastern Shore, annual skipjack races in Deal Island and Cambridge still draw up to about 10 competing skipjacks each year. But those locales are too far for some of the upper Bay-based vessels. The Sandy Point location will not only bring the skipjacks back to their Chesapeake Appreciation Days roots, but is also an accessible course for a wide range of skipjacks. 14-15 of the surviving skipjacks are expected to be at Sandy Point for race weekend.
This historic gathering of boats will include skipjacks that have been retrofitted for commercial cruises, like the Wilma Lee from the Annapolis Maritime Museum, the H.M. Krentz out of Chesapeake Bay Maritime Museum in St. Michaels, and the Nathan of Dorchester from Cambridge. It will also include privately owned skipjacks, most of which are still powered by motorized pushboats. Some, like the Han Em Harv (formerly known as the Anna McGarvey) are still commercially dredging for oysters today. One, the Messenger, is coming all the way from Onancock, Virginia.
Fleet Captain Shawn Ridgley captains the privately owned, circa-1906 skipjack Ida May, which has been in the same family for three generations. He says this event will serve to highlight the skipjacks by bringing them to “new eyes” on the Bay’s western shore.
Susan Schneider, organizer with the event’s nonprofit partner Skipjack Heritage, Inc., points out that the skipjack is Maryland’s state boat, so it’s only appropriate for it to be celebrated in Maryland’s state capital. “Only a handful of states even have a state boat,” Schneider says.
Ridgley wants to show people in Annapolis that “this fleet really does exist,” he says. Some people may not realize there are skipjacks still actively harvesting in the commercial oyster industry. “It isn’t just a nice boat silhouette to put on your business sign,” Ridgley quips.
Both Saturday and Sunday of Skipjack Heritage Days will offer visitors a slice of skipjacks past and present. On Saturday, the privately-owned boats will be lined up along the bulkhead, as longtime captains tell stories of the skipjacks’ heyday. The skipjacks (and a pair of classic Chesapeake Bay buyboats) that are commercial cruise vessels will offer boat rides for visitors.
Sunday is the main event: the racing. A parade of sail will be held at 11 a.m., and the Skipjack Heritage Race begins at noon. Seeing the fleet of skipjacks under sail will be a treat for spectators, since Sandy Point provides ample views of the race course. The start line will be between Sandy Point Shoal Light and the Maryland Department of Natural Resources buoy tender, A.V. Sandusky, which you may remember broke ice in the area just this past January. The boats will round Baltimore Light and return to the start line. Sandy Point’s East Beach, Ridgley tells us, will be an excellent viewing location as the skipjacks go back and forth.
Skipjack Heritage Days is a perfect marriage with the Maryland Seafood Festival, another annual celebration of Chesapeake Bay heritage taking place at Sandy Point the same weekend. The festival, which runs Saturday, Sept. 13, 11am – 7pm and Sunday, Sept. 14th, 11am – 6pm, brings back favorite traditions including the Crab Soup Cook-off, seafood eating contests, and popular regional bands like Jimmie’s Chicken Shack and the Naptown Brass Band. A Mermaid and Pirate Parade, BMX stunt bikes, crafts, and inflatable bounce houses will appeal to the kids.
There will be a Champions of the Chesapeake hands-on education area made up of local nonprofits furthering Bay causes, like Blacks of the Chesapeake, Chesapeake Bay Foundation, and the Chesapeake Bay Trust.
Those who buy a Seafood Festival ticket have access to all activities in the main festival grounds and at the marina, including the public skipjack sails on Saturday (at no additional cost).
“Skipjacks are living history,” says Schneider. “They’re iconic to our region, and this festival offers a rare chance to experience them up close.”
Jeremiah Batucan, founder of Peake Events, which partnered with ABC Events to put on the Maryland Seafood Festival, spoke to the synergy between the seafood festival and the Skipjack Heritage Days. “It’s truly ‘dock to dine’, he says of the festival’s oyster-dredging skipjacks and the seafood being served up.
Festival tickets start at $15 (free for kids under 12). Find them here.
