Fun Loving, Family Friendly Pirates in Rock Hall

For the 4th year in a row, the sleepy waterman’s hamlet of Rock Hall, Maryland is taken over by the Pirates and Wenches Fantasy Weekend, this year on August 12, 13 and 14.

Getting bigger and better each year, the festival is full of activities for everyone, including the children or “little swashbucklers.” There is a dinghy race, a Sea Shanty Sing-a-Long, a costume contest, even a rum tasting (for the adult pirates of course!)

Here are Patty and Dave, someĀ pirates guests who stayed with us last year and posed for our camera before heading off to enjoy the festivities:

If you’ve been to visit us before, then you know that we are big fans of Blue Crab Charters out of Rock Hall. Captain Mark Einstein and his First and Only Mate (I love that!) Suzanne Einstein take up to 3 couples on their sailboat, 5 times a day all summer long. Well, as if that’s not enough to keep them busy, they are also heavily involved in the Pirates and Wenches weekend. Look for them if you go and tell them we sent you!


Toasting glasses of red wine in front of fireplace



Chestertown is the perfect location for a memorable staycation! Stay any 3 consecutive nights and receive 50% off your third night.

*Valid thru March 3, 2022 on new reservations only. Not valid with other special offers or third-party booking sites.