One of the biggest weekends of the year here in Chestertown is coming up soon: “Down-rigging”, denoting the end of the sailing season, has over the past many years grown to be a weekend long festival filled with tall ships, music, food, fireworks, lectures, races, films, classic cars and wooden boats. And fun! Always the last weekend in October, this year the 22nd annual event runs from the 28th to the 30th.
Each year it seems to get bigger and better, with more and more things to do and something for everyone. This really is a fun festival. It’s no wonder this is the second busiest weekend of our year. Only Memorial Day/Tea Party weekend rivals it. The weather almost always cooperates, and stuff is happening all day and into the night. If you aren’t on a tall ship, the Music Village is the place to be to enjoy your favorite regional food and drink while listening to some of the best bluegrass bands in the county.
Tour the Sultana, ride the Packet, watch the Cocktail Class Racers. What the heck are these things?? Come on down to the land of pleasant living and find out for yourself. We promise you’ll be glad you did.
Join us at our Maryland bed and breakfast and join the fun! After an exciting day at the docks, unwind in one of our cozy rooms, suites or cottages and enjoy a glass of local wine.