Arrrrg You Excited for a Weekend of Pirates and Wenches in Rock Hall?

pirate-themed decorated rafts at pirates and wenches in rock hall

Pirates and Wenches in Rock Hall is one of the most anticipated events of the summer. The area is turned into a town-wide theme party of patrons plundering for awards in costume contests and treasure hunts. Visit August 9th through August 11th in your best pirate attire for this thrilling celebration. And, if you’d like to learn more about what there is to do in Rock Hall, take a look at our complimentary Vacation Guide. We provide insights on more of our favorite events, restaurants, and attractions that you need to experience while visiting the Chesapeake Bay area. Join us and begin your adventure.


The Rock Hall Vacation Guide


Everything About Pirates and Wenches in Rock Hall

Day One

Pirates and Wenches Fantasy Weekend starts on Friday, August 9th. One of the first activities you can enjoy is a rum tasting at the Osprey Point Restaurant. For just twenty dollars, taste five different flavors and also receive a helping of gumbo. While you take in the grog and grub at this Rock Hall restaurant,  live music sets the mood for the exciting event.

The next activity of the day is at Bay Wolf Restaurant. Stop in to experience the Sea Shanty Sing-A-Long, which features pirate performers and prizes for the best pirate hat and joke. What’s even better, they also have some of the most delectable Chesapeake Bay Blue Crabs to snack on while enjoying the festivities!

Day Two

The day begins with a viewing of the decorated dingy flotilla gathered within the deep blue waters. All of the vessels are fighting for a chance to have their name engraved on the Gray Beard Cup! It’s amazing to look at so many boats decked out in authentic pirate gear.

Next, it’s time for a Caribbean beach party on Rock Hall Beach. Spend your afternoon basking in the warmth of the sun, sampling more local grub and grog, and dancing to the tune of live music. Make sure you stick around long enough to hear the judges announce the winner of the dinghy decorating contest!

Saturday’s festivities don’t stop there. In the evening, go to Waterman’s Crab House to attend the Buccaneer’s Ball featuring some fantastic live entertainment. It’s here where you’ll see the crowning of the king and queen, and you’re sure to have a chuckle while watching the Graybeard Look-A-Like costume contest. This is a great way to end the second day of the festival.

Day Three

On the final day of Pirates and Wenches Fantasy Weekend, the “Talk Like a Pirate Contest” commences. At this event, with such great impressions and costumes, you may feel like you’re amongst real pirates!

Then, the thrilling, town-wide treasure hunt begins. The treasure hunt is unique because it’s woven all throughout Main Street in Rock Hall and includes participating businesses. You’re given 2-hours to locate the hidden goods somewhere amidst the bustling activity of the festival. Or, meet at the gazebo to see who will be claimed the winner of the secret prize.

Inn at Huntingfield Creek is Right Around the CornerIsland Cottage Bedroom

Our inn is a 3-minute drive from the heart of Pirates and Wenches in Rock Hall. If your whole pirate crew is planning on attending, we suggest reserving a few of our spacious cottages. Island Cottage offers unique treasures of its own, including a spacious living and dining area, a relaxing whirlpool tub, and a plush, king-size bed. For the ultimate adventure in the Chesapeake Bay area over this thrilling weekend, join us at Inn at Huntingfield Creek.

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