Upper Eastern Shore
The Eastern Shore was given its name by Captain John Smith, who sailed from Jamestown in the summer of 1608 to explore the Chesapeake Bay as far north as the Sassafras River. Kent Island was one of the initial settlements starting about 1631, and for three hundred years thereafter, the Eastern Shore has thrived on its agricultural and seafood base, and prided itself on its distinct and independent ways.
The coastline is dotted with historic waterfront towns and rolling farmlands where fresh and salt water meet for fishing and boating enthusiasts, cyclists, birders, and nature lovers. A bike ride through the rural landscape may take you to Chestertown, where you can rent a kayak to paddle the Chester River for a chance to see a great blue heron, an osprey, or an eagle. For more bird watching, visit The Eastern Neck National Wildlife Refuge.
The fishing, crabbing, and sailing town of Rock Hall is known for its seafood restaurants and natural wildlife preserves. Visit The Rock Hall Museum or Waterman's Museum to learn more about oystering and crabbing.
Take day trips to Annapolis and Baltimore and know that the welcoming hospitality of the innkeepers at our Maryland Bed and Breakfast Association member inns awaits you after a busy day.