Whether you are exploring its history or shopping the red-brick, tree-lined sidewalks of Historic Downtown, you will quickly fall in love with Chestertown.  Once a thriving colonial port town, Chestertown is a well-kept historic treasure, located on the shores of the Chester River and was recently named one of America’s Distinctive Destinations by the National Historic Trust, a designation for unique and lovingly preserved communities.  It was also recently designated a Maryland Main Street.

You will enjoy the Geddes-Piper House Museum ca. 1784, guided and self-guided historic tours, the Schooner Sultana, 1768, Prince Theater’s live performances, specialty and antique shops, art galleries and studios, restaurants and more.

So if your looking for a waterfront getaway, close to home, this scenic peninsula on the Chesapeake Bay is the ticket for a perfect escape.