Southern Bay Cruisers Race for the Cape Charles Cup

The Black Widow sails across the Chesapeake Bay Saturday during the 15th annual Leo Wardrup Memorial Cape Charles Cup. Wardrup was one of the founding members of the regatta and an owner of the Black Widow . Photo: Clara Vaughn

It’s billed as the “cruising event for serious racers and the racing event for serious cruisers.”

That, and its renowned afterparty, is what drew hundreds to the Leo Wardrup Memorial Cape Charles Cup last weekend.

More than 85 sailboats registered for the 15th annual event, which carries cruisers and racers alike from Norfolk to Cape Charles and back during the two-day race.

Not only is it the premier August social event for crews in the Southern Chesapeake Bay, but the regatta by Broad Bay Sailing Association raises thousands of dollars to send underprivileged children sailing each year through the Sail Nauticus program.

“It’s a very acknowledged social event that people really enjoy, and that has as much meaning as the racing part of it,” said Cup Fundraising Chair Carl Gade.

“It has to be a fun thing,” said Bill Barnes, a Cup committee member. “If you’re not having fun, you shouldn’t be doing it.”

 Leo Wardrup Memorial Cape Charles Cup committee members, from left, Ben and Christina Ritger and Bill Barnes pause for a photo while watching the race Saturday. Photo: Clara Vaughn
Leo Wardrup Memorial Cape Charles Cup committee members, from left, Ben and Christina Ritger and Bill Barnes pause for a photo while watching the race Saturday. Photo: Clara Vaughn

The Cape Charles Cup began more than a decade ago with a conversation between Barnes and friends.

“I was whining because we didn’t have longer, better races,” said the then-newcomer to sailing. “The two men I was sitting with were Leo Wardrup and Sonny Smith.”

Wardrup, a naval officer and longtime member of the Virginia House of Delegates, agreed to raise funds for a new regatta if Barnes organized the event, and the Cape Charles Cup was born.

After he passed away in 2014, organizers named the race in Wardrup’s memory.

Founding the race with Lou Tuttobene, John McCarthy and Scott Almond, the duo drew more than a dozen sailboats the inaugural year. The regatta has since fallen into favor with cruisers and racers alike and now pulls a crowd of more than 70 boats, thanks to its nominal entry fee and renowned afterparty.

Festivities begin Friday before the race with a skippers’ meeting complete with a barbecue dinner, beer and live music at Bay Point Marina, in Norfolk. On Saturday, rolling starts launch from Norfolk’s Little Creek and crews race to Cape Charles, on Virginia’s Eastern Shore.

“We have different classes of sailboats and they sail at different speeds— they have different handicaps,” said Christina Ritger, the Cup’s chair-elect and longtime participant. “These starts are based upon where you are… in your boat’s abilities: The fastest boats start first.”

“There’s literally room for everybody in the regatta,” she said.

Saturday night, hundreds gather on Cape Charles’ docks for an awards ceremony and afterparty before racing back to mainland Virginia the next day.

With the regatta’s growing popularity, sponsorship dollars surpassed costs of hosting the event and a partnership with Sail Nauticus was born.

Each year, the cup helps fund the nonprofit program, which helps underserved youth in Hampton Roads get on the water to learn about science and develop skills from swimming and first aid to teamwork, leadership and communication through sailing.

“It benefits all kinds of children from all kinds of backgrounds to get on the water,” Ritger said.

On Sunday, crews head home, but the camaraderie continues throughout the year, the Cup’s Vice Commodore Eric Brinsfield said.

“I met several people from this group when I got my captain’s license and they encouraged me to join,” he said. “It’s the best thing I’ve ever done.”

“You meet a lot of people competing,” Brinsfield said. “I’ve met the best people here.”

Click here for the 2018 Leo Wardrup Memorial Cape Charles Cup results Day 1, and click here for Day 2 results.

Learn more about Sail Nauticus here

-Clara Vaughn