Now, for one weekend each August, the Kent County town, population 1,500, give or take a soul or two, emblazons its streets with everything pirate. And these folks take their swashbuckling seriously: There are plenty of “arrrrs” to go around.
Truth be told, the weekend wasn’t meant to be much more than a reason to dress up, according to Mark, who’s no stranger to the high seas as captain of Blue Crab Chesapeake Charters. (Suzanne is first mate.) As the event’s web page states, it’s “just for fun—totally pointless.”
“Initially, we simply had a vision of lots of costumes and fun for the whole family in a small town with a big heart,” he says. “From there, the idea took off and became quite a spectacle, with the various events and activities.”
It is, indeed, a spectacle, starting with the skull-and-crossbones flags scattered among the towering cornfields on Route 20 as you drive into town. You don’t have to squirrel away your jewels and wallet in the glove compartment, though. There are no Dread Pirate Roberts or One-Eyed Willies to swipe your loot.
There are only nice pirates in attendance, including Valhalla’s Pirates, the plundering, pillaging, and plank-walking entertainment crew that performs re-enactments of the Einsteins’ wholly fictitious (and wholly riotous) account of Rock Hall’s pirate history and the Legend of Graybeard, which sets the theme for the weekend.
(Pirates did, in fact, sail and pillage the Chesapeake Bay hundreds of years ago, just not around Rock Hall.)
A Sea Shanty Sing-A-Long at Baywolf Restaurant on Friday evening kicks off the weekend and, come Saturday, Rock Hall will have transformed itself into one big seaside festival.
The decorated dinghy race (think inflatable dolls tied to masts and more pirate flags), which truthfully is more of an aimless drift, is the highlight of the day. It casts off from the party at the Harbor Shack and culminates at Rock Hall beach with a Caribbean-style soiree.
On land, local pirate and Celtic bands, artisans, and merchants fill up Oyster Court Village and Main Street Marketplace, letting lubbers eat, drink, dance, shop, take pictures with parrots, get their faces painted, and generally be merry.
There’s a lot going on, so be sure to pick up a map of times and locations for each activity. And if you forget to dress up (costumes are not required, but they are strongly encouraged), you can snag authentic pirate or wench attire at the living-history pirate encampment. Or simply purchase a skull-and-crossbones bandana and wooden sword from the local scout troop, like I did.
Now, one might be compelled to compare Pirates & Wenches to the Maryland Renaissance Festival, as it, too, draws people with a niche fascination for a similar era and dress code from all over the country.
Don’t.
Uttering that comparison to Captain Charles W. Black of Valhalla’s Pirates draws solemn head-shaking and is, in effect, blasphemy. The parallels are there, what with all the puffy shirts, petticoats, and trilled R’s, but the cult of pirate (and that is what it is) tows a different party line.
One woman, ahem, wench, Kim Maur (also with Valhalla’s Pirates), says pirates have been in her family for generations. Still, she got into it for the sword fighting.
“I met someone at the gym who said they were reenacting, and I laughed at it,” says Maur. “And they said, ‘But we do sword fights,’ and I said, ‘Sword fights? I’ll try it!’” she recalls.


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