Beautiful scenery, charming mom-and-pop shops, and a vibrant coastal culture are just some of the reasons why the Eastern Shore of Maryland is the perfect year-round destination. Throughout the year there are also fun events, festivals, and classes you can attend to make your Maryland getaway even more transformative! There are lots to choose from, so we’ve listed some of our favorite Chestertown, MD events below for you!

Join Us February 23 for a Wedding Open House

Discover the magic of our venue, meet our event team and vendors, explore the ceremony and reception spaces and guest rooms.

[register_now]

Join us for a Murder Mystery Weekend! 

March 14-16 take part in the whodunnit festivities!

Book Now

Beat the Winter Blues at Brampton 1860!

        Any 2 nights Sunday-Thursday, for 25% off your second night. Any 3 nights, for 50% off your third night. Stays through March 31.

Book Now