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Setting Sail for Fun

Rock Hall pirate festival is ‘arrgh-uably’ one of best in Maryland

October 2023

Three local revelers, dressed up and ready for Pirates & Wenches Weekend in Rock Hall, Md. (Photo by Gregg MacDonald)

Although it takes place annually in mid-August, Pirates & Wenches Weekend in Rock Hall, Md., has its roots firmly set in Halloween.

Pirates & Wenches Weekend is one of Maryland’s most anticipated annual family-friendly celebrations. (Photo by Gregg MacDonald)

The annual nautically themed event — now in its 16th year — began in 2007 when Captain Mark Einstein and his wife, Suzanne, were at Rock Hall’s Waterman’s Crab House restaurant for a Halloween costume contest.

“The idea for Pirates & Wenches Weekend was conceived as we watched pirate after pirate entering the tent for the contest,” Captain Mark recalls. “Suzanne and I had been inspired by the wonderful experience we shared while serving on Rock Hall’s Tricentennial Committee during the previous two years. We were mightily impressed by the way pretty much everyone in town came together to support and celebrate the town’s 300th birthday.” It was then that the idea for a pirate-focused weekend, including a Buccaneer’s Ball, was born.

After bringing the event to fruition, for the next 10 years the Einsteins took the helm of the annual event, evolving it into one of Maryland’s most anticipated annual family-friendly celebrations. Rife with puppet shows, costumes, cannon fire, music, juggling acts, decorated homes and decked-out flotillas, there’s something at Pirates & Wenches Weekend to help push everyone off the plank into an early Halloween season.

For more, go to rockhallpirates.com.