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!

Fall Wine Country Escape

Enjoy the perfect vineyard getaway this fall with a wine-tasting flight and cheese platter at award winning Crow Vineyard and Winery, dinner for two, and more! Only available September 1- October 31, check your dates now!

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