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!

Take a midweek getaway!

Savor the lush and tranquil surroundings of the Brampton Inn with a 3-day stay and get away from it all. Book two-nights and get your third night FREE Sunday through Thursday!

*Offer valid Sunday-Thursday thru August 31, 2023, in select rooms and cottages. New reservations only. Not available on third-party sites. Discount applied to least expensive night and cannot be combined with other offers.

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