Widow's Walk Inn

The Widows Walk Inn B&B is located in the Historic District of Chestertown, on Maryland's Upper Eastern Shore, only 1 1/2 hours from Washington, Baltimore and Philadelphia.  Situated on High Street, the Inn is within a short walking distance of the Chester River, Washington College, many homes and buildings of historic significance, as well as quaint gift shops and fine restaurants. There are many area activities including Boating, Hunting, Golfing, Fishing, Biking, Birding, Antique and Boutique Shopping.  Award winning restaurants as well as casual eateries can be found in Chestertown and throughout the County.  Click on the links below for detailed information. At the Inn, you will find comfortable lodging with the atmosphere and warmth of a family home.  The Inn is furnished with an eclectic collection of antiques and family treasures.  While our parlor is equipped with cable TV, table books and games, and offers a cozy retreat for conversation, the Inn also has four porches, including a screened rear porch and the large front porch complete with rocking chairs and a swing.  You are also invited to sit and relax on an attractive patio surrounded by gardens; the perfect place to discover a great book.