Downrigging Weekend is Almost Here!

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 15 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 16th 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.  But this year it’s really gone to the dogs…. DOCK DOGS, that is!  New this year, folks can head across the Chester River to Kingstown Farm, Home, & Garden and watch a canine aquatic competition.  Think your dog can jump the farthest?  Register and bring her down!

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. Food and drink are abundant.  On both Saturday and Sunday, visit the Chesapeake Wine Trail pavilion for  a wine tasting from 3 of our esteemed local wineries.

Tour the Sultana, ride the Packet, watch the crab skiff rumble.  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 suites and enjoy a snack by the fire.

Brampton Inn Gift Certificates

Give the Gift of a Luxury Travel Experience!

Now thru December 31, 2021, when you buy a Brampton Inn Gift Certificate of $500 or more, you’ll receive a special code worth 10% off your next stay! Discount valid for stays thru December 31, 2022. Discount on room rate only, cannot be combined with other offers or third-party bookings. Not transferable. Must book direct at or call.

See Gift Certificate Information