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!

Midweek Autumn Escape Special! Stay 3+nights Sun-Thurs, enjoy 30% off 3rd night through Oct 30
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Join Us September 7 for an Open House! Enjoy an enchanting afternoon and learn about renting the Inn for your special occasion.
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Join us for a Wine and Small Plate Tasting Dinner on Sept 18. Overnight guests save 15% off room!
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or for Dinner only
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