Getaway Guide: Pirate Weekend

August 1, 2013 8:00 AM

(credit: Jay Lloyd)

Reporting Jay Lloyd

So, you want to be a buccaneer? Then mark the date and set a course to rendezvous with some of the saltiest sailors to voyage under the black flag! The place is Rock Hall, Maryland on the eastern shore of the Chesapeake Bay. The dates are August 9th to 11th, when this rollicking port becomes a buccaneer haven for more than 5,000 revelers in full pirate regalia. Show up for a pirate dinghy assault and grog party on the beach, then craft your own pirate rig and prepare to be judged for best costume at the Buccaneer’s Ball, where there’s lavish loot for winners. Here’s where you make your mark and cast off for a fantasy adventure into the swashbuckling past. – Jay Lloyd


Rock Hall, Maryland
August 9th, 10th and 11th

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Events and activities for adults and kids cram the calendar and take place within a walkable area from Main Street to the Harbor and nearby beach. The events for adults include:

Friday night: Join in the Rum Tasting at the Osprey Point Inn and a Pirate Sing-along at the Bay Wolf restaurant on Rock Hall Avenue.

Saturday: Both children and adults can wander the pirate encampments off Main Street and watch demonstrations of buccaneer swordplay skills, shop for pirate swag and garb and feast on local fare. At the harbor, crowds gather to watch a decorated dinghy parade as the flotilla heads for a point just off the town beach. Afterwards, dig into beach party grub and grog while cheering on the boisterous dinghy crews as they race and battle their way to shore. There’ll be Caribbean music, boat rides, crafts and games, too.

Saturday night: The costumed Buccaneer’s Ball fills the Waterman’s Crabhouse deck with the music of corsairs and costumed revelers vying for prizes and hoisting tankards of ale and rum toddies while gnawing on steamed crabs or slurping Chesapeake oysters. Admission is free, but pirate weekend “skippers” would like the crew to at least buy a raffle ticket to help offset the cost of the booty being divvied up. Prizes will be shared by those who are tricked out in the most intriguing pirate garb. One guy last year showed up with a real live parrot on his shoulder – a small one, but it looked like a parrot at least!

(credit: Mary Lloyd)

(credit: Mary Lloyd)


You can spend hundreds for a pirate getup at a re-enactors shop or a modest sum at a Halloween costume store. I prefer to make my own. It may not be grand or in true Captain style, but it does the trick. Just wear a Breton sailor shirt or a woman’s blouse with a sash and headband. You can add an eye patch, a bit of bling and a sword, axe or faux flintlock if you wish. Then swagger down Main Street, belly up to a bar and let your imagination run wild!

(credit: Jay Lloyd)

(credit: Jay Lloyd)



Period furnished rooms in a stately inn with gorgeous views of pristine Swan Creek. There’s a first rate restaurant and intimate bar here as well.


The Black Duck Inn is a comfortable, reasonably priced B&B directly on Rock Hall Harbor and just a short walk from all the weekend activity. There’s a great Sunday breakfast and brunch at the waterside café.


Located on Swan Point, the Moonlight Bay Inn has a spectacular view of the sunset on the Chesapeake Bay. The rooms are tastefully furnished and reasonably priced. Breakfast is a treat.


The Marina features clean, brightly lit motel accommodations in a nautical setting and all rooms directly face the bay. This spot is reasonably priced and a short walk to most of the activities.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Since it’s a major weekend, expect restaurants to be crowded, but looking for a table during off peak times will let you sample some of the best food in Rock Hall. For harbor views and outdoor seating check in at the HARBOR SHACK and WATERMAN’S CRAB HOUSE. BAY WOLF RESTAURANT, OSPREY POINT INN and SWAN POINT INN are known for their amazing kitchens, and all are within walking distance of the harbor. A jitney service also stops at all restaurants, marinas and event locations.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


From Philadelphia, take I-95 South to I-896 in Delaware. Follow 896 South to Route 301 South. Continue south on 30. Take the exit for Chestertown and Galena, then make a right at the exit and follow 290 to Route 213 at Galena. Take 213 South to Route 20 West in Chestertown. Continue on Route 20 to Rock Hall. If your tires get wet, you’ve gone too far. The trip takes about two hours from Center City.

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