Fans turned out to see dozens of deadrise boats race to the finish. All photos courtesy of York County’s Department of Economic and Tourism Development.
Battle of Yorktown: Workboat Races Expand into Weekend-long Festival
The sight of a graceful deadrise boat plying Chesapeake Bay waters is timeless: a reminder of how many people in waterfront communities still make their living the way their ancestors did. But the sight of more than 40 deadrise boats roaring up the York River, racing for all they’ve got? That is something to behold.
When the Yorktown Workboat Races return this month, the event will be part of an expanded, weekend-long festival celebrating Chesapeake Bay watermen’s heritage—spearheaded by the group Workboat Life. Spectators will see the clean lines of the Chesapeake Bay deadrise put to the test as watermen compete for class awards. They’ll also see an impressive display of model workboats built from scratch and other art, plus interactive displays on Bay workboats, the seafood industry, and the Bay at large.
The Yorktown Workboat Races were a longtime tradition on the York River that died out in 2005. Workboat Life brought racing back in 2024 after a 19-year absence, and it was a smashing success for the watermen, locals, and Yorktown visitors. This year, Workboat Life and the town are putting together an even bigger event.
Workboat Life began as a Facebook group for Virginia watermen in 2018, and in the last seven years it has swelled to a community 36,000 strong that stretches well beyond the Bay. Founder Allen Holston, a 20-year waterman himself, says, “I know watermen and I know how much they appreciate having a social media presence to communicate, share stories, discuss issues, see pictures of their boats and to see them in action.”
After he retired, Holston began making videos of watermen working and posting them on the Workboat Life YouTube channel. Not only did it resonate with Virginia watermen, word spread quickly. “We started local and it started growing, and before you knew it we spread all along the East, Gulf and West coasts and then went international. Workboat Life has become a communication hub for the industry. All [sectors]… regulatory, scientific, environmental, ocean fisheries, inshore fisheries, seafood processors, packing houses, marine supplies, the watermen themselves… everyone participates.”
Seeing such strong interest, Holston created spinoff Facebook groups like Working Women of the Water to recognize female harvesters, Watermen Remembered to honor community members who have passed, Old Salt for “old timers” to tell their stories, and Oysters for Sale to give the industry a selling platform.
Thanks to encouragement from Yorktown to grow its presence at events, Workboat Life became a nonprofit organization in 2023 with Holston as its president. Its mission is to “promote and celebrate the history and continued use of the Commonwealth of Virginia’s official boat designation, the Chesapeake Bay deadrise.”
Holston says the 2024 return of the Yorktown Workboat Races came because Workboat Life wanted the watermen to have a chance to “gather and have some fun.” It also stimulated Yorktown’s economy, filling hotels, shops, and restaurants.
Painstaking work is showcased at the model boat show.
This year, the first day of the festival is all about engaging the public with “The Waterman’s Way”. Displays, demonstrations, and activities for children of all ages will be offered Saturday, May 31, from 10.a.m to 3 p.m. at the Yorktown Watermen’s Museum. That evening the organization will hold a private Saltwater Heroes Appreciation dinner for watermen to kick back.
Sunday, June 1, begins with the Workboat Model Show and Art Show, running 11 a.m. to 4 p.m. Talented model builders will display their miniature vessels and compete in the categories of skiff, Fox Hill pound boat, open deadrise, deck boat, rigged, and remote controlled model boats. Paintings and photography will also be displayed and judged.
The festival’s main event, the Yorktown Battle of the Boats, begins at 12:30 p.m. with a blessing of the Fleet and recognition of a handful of Bay buyboats that are celebrating their 100th birthdays this year. The workboat competitors will then parade past the Yorktown waterfront. The deadrise races begin at 1:30 p.m., with a 4 p.m. awards ceremony for the fastest boats.
It’s all play, no work, for the crews in the Yorktown Workboat Races.
This year’s Yorktown Workboat Races lean into the town’s American history, going way back to the Siege of Yorktown, the final battle of the American Revolutionary War. Coining this year’s deadrise races “Yorktown Battle of the Boats 2025”, Holston points to the connection between Virginia’s important role in colonial independence and the beginning of the commercial seafood industry. Here is Holston’s historical retelling of the showdown at Yorktown. It begins as Admiral François Joseph Paul, Marquis de Grasse Tilly, heads to the Chesapeake Bay to support General George Washington’s assault on the British.
De Grasse’s fleet was loaded with 3,000 French troops on 37 ships of 28 large battleships, 7 frigates and 2 cutters. Washington directed his troops to Yorktown to surround General George Cornwallis, who intended to knock Virginia out of the war.
De Grasse arrived at the Chesapeake, saw no British fleet and sailed up the James River the morning of Sept. 5, 1781, to unload the troops to take positions around Cornwallis. Several of his ships’ officers were ashore, offloading supplies, when the British fleet arrived. Still, British Admiral Thomas Graves failed to take advantage of the vulnerable position the French were in. De Grasse had time to rush his fleet out of the James and organize into a line of battle.
This 19th-century painting, owned by the U.S. Navy and on display at the Hampton Roads Naval Museum in Norfolk, depicts the battle. Image from National Park Service.
At 4:15 p.m. the Yorktown Battle of the Boats began for control of the Chesapeake Bay. Two hours later as the sun set at 6:30 p.m. they disengaged to assess the damage. Admiral Graves realized his fleet had taken too much damage to reengage and both fleets drifted south a couple days. Seeing no more action from the British, Admiral De Grasse sailed into the Chesapeake as victor, with control of the Bay. This left General Cornwallis helpless with no support and no other choice, but to surrender to General Washington.
This battle was a decisive blow that resulted in American and French troops securing independence from the British Crown. The colonies soon became states, and Virginia’s seafood economy remained a large part of the economy. Many of our waterman families today are direct descendants from this beginning.
Thankfully, the “battle” these modern watermen will enter into on June 1 is not a matter of war; it’s all for fun. And from Holston’s perspective, they deserve some fun—and some recognition.
“These Saltwater Heroes, the Virginia commercial watermen, are very competitive and work hard year-round in all conditions putting local, fresh seafood on your table while feeding their family and feeding America!”
Find more details on the Yorktown Workboat Races Battle of the Boats 2025 and surrounding events here.
Note: If you want to dive deeper into the history of these vessels, workboat historian, author, and longtime Chesapeake Bay Magazine contributor Larry Chowning will be on hand during Sunday’s events. He’ll be signing his 2024 book Chesapeake Bay Deadrise Boats and other books he has written about historic boats and the seafood industry.
