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Home > About the Chesapeake > Places and People > Bay Songs and Beer (from Window on the Chesapeake)
Bay Songs and Beer (from Window on the Chesapeake)

Image from Window on the Chesapeake
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Like a great graceful white bird, the schooner Woodwind has flown across the Chesapeake Bay and back, and she’s sailing into the sun setting over the Statehouse dome in Annapolis when Jeff Holland takes the wheel and eases into his epic poem, Blood of the Bold Picaroon. Until now, the boat’s cargo of tourists haven’t been paying much attention to Jeff and his cohort Kevin Brooks, better known as the Annapolis-based singing-songwriting team of Them Eastport Oyster Boys. Perhaps the visitors can be forgiven; few sights are as distractingly lovely as Annapolis Harbor at sunset from the deck of a lively sailing ship. But as his voice slowly builds over the water, Jeff’s rollicking story of the
Cover from Window on the Chesapeake
This story is an excerpt from Window on the Chesapeake by Wendy Mitman Clarke. To order this book, visit the Mariner's Museum.
pirate named Captain Doubloon—a tale loosely based on pirate Richard Clarke’s plan in 1707 to sack Annapolis and steal its arms and ammunition—pulls them in. “His veins carried nothing but water and ice;/Yes, a cold-blooded creature he happened to be,/ With no trace of mercy or charity;/ He’d capture a ship, make the crew walk the plank,/ And he’d never say, ‘Please,’ ‘You’re welcome,’ or ‘Thanks.’ ’’ …Once the tale is over, Jeff exchanges the wheel for his baritone ukulele, the Oyster Boys break into a lively calypso song about a blustery day sailing on the Bay, and the crowd is hooked for the duration. “It’s a lot of work because it’s hard to grab people’s attention,” Jeff says of their weekly performances on Woodwind, one of the Oyster Boys’ many gigs. “But it’s really our creative time,” Kevin says. “We go out for two hours, meet people from all over the world and show them why we love this place, that this is why we’re here.”

Why they love this place—the Bay broadly, and Annapolis’s maritime heart, the neighborhood called Eastport, more specifically—has to do with the details. Worn-out boat shoes. Smelly wet dogs who shake all over you. Crabbing. A history richer than a pirate’s buried treasure. Maryland beaten biscuits. A good sailors’ pub. A lovely white workboat, lonely and old. The sight of the sun setting over the water. A fine breeze in the evening.

Whatever their topic, the songs are meant to deliver their message gently, humorously, almost subliminally, Jeff says. “The idea is to find out what it is that makes this place special and pick it out and celebrate it,” he says, “and I think people realize that if something is worth singing about, it is special.”

It’s no small feat to pack all that joy and laughter and culture and history into a short song and get it across to a bunch of strangers on the swaying deck of a sailboat. But beers in their pockets and songs in their hearts, Them Eastport Oyster Boys sure look like they’re having fun trying.


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