This area, located in the Upper Eastern Shore region, was once a busy port for Colonial settlers. The history of the area has been well preserved. As you walk the quiet cobblestone streets, you will find many 18th century homes and churches that have been beautifully restored. There is much to see in Chestertown. Take a day to visit the wonderful antique stores, eclectic galleries, and fantastic restaurants. Home to Washington College, Chestertown is the perfect home base for exploring the Eastern Shore of Maryland.
From delicious seafood to beautiful views and calming waterscapes, you will quickly fall in love with all that this area has to offer. With many lodging options in the Eastern Shore area, let the Maryland Bed & Breakfast Association help you find the perfect inn to make your time in Chestertown unforgettable.