The charming town of Chestertown, Maryland, is a gem nestled in the heart of the Eastern Shore. Spend your days here tasting delicious coastal cuisine, touring Washington College, and relaxing in nature. 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 to celebrate. Chestertown is an unforgettable destination along the Eastern Shore of Maryland. The area is home to countless outdoor activities, making it the ideal place for wildlife viewing, hiking, boating, hunting, and more. As a guest of Brampton Inn, you are just minutes away from the Chester River and the Chesapeake Bay. It’s the ultimate setting for your next romantic getaway. Whether you prefer country favorites, fantastic seafood, or light, farm-to-table bites, you’ll find exactly what you’re craving on the Eastern Shore of Maryland. Our guests love the region’s bayfront eateries, intimate cafes, and fine dining spots. It’s time you experienced it for yourself!