The Eastern Shore: Places to Explore


  • Berlin

    Berlin—named not for the German city, but evolving from Burleigh Inn, a Colonial-era way station—is a short drive from Ocean City, yet it could not be more different. Magnolias, sycamores, and ginkgo trees... Read more

  • Blackwater National Wildlife Refuge

  • Cambridge

    Once upon a time renowned resident Annie Oakley would shoot waterfowl from the ledge of her waterfront home here. Today graceful Georgian, Queen Anne, and Colonial Revival buildings abound, and with an... Read more

  • Chesapeake City

    As it's a town split dramatically in two by the Chesapeake and Delaware (C&D) Canal, Chesapeake City homes and businesses face each other across the busy waterway. Those sitting at the restaurants... Read more

  • Chestertown

    Second only to Annapolis in its concentration of 18th-century houses, Chestertown was a major international port in Colonial days: a tall, brick customhouse continues to dominate the High Street waterfront... Read more

  • Crisfield

    In William W. Warner's study of the Chesapeake Bay, Beautiful Swimmers, Crisfield was described as a "town built upon oyster shells, millions of tons of it. A town created by and for the blue crab, Cradle... Read more

  • Easton

    Well-preserved buildings dating from Colonial through Victorian times still grace this affluent, genteel town. Fine art galleries, high-quality antiques shops, and gift boutiques sit side by side along... Read more

  • Furnace Town

  • Grasonville

    Follow the scenic byway, old two-lane Route 18, across Kent Island and over an aging drawbridge across Kent Narrows to reach quiet Grasonville. The modest homes and shops of the town are a pleasant alternative... Read more

  • North East

    Uncommon neighborliness along a main street of antiques and collectibles shops and homey eateries gives Cecil's riverside county seat its welcoming charm.... Read more

  • Ocean City

    Stretching some 10 mi along a narrow barrier island off Maryland's Atlantic coast, Worcester County's Ocean City draws millions from neighboring states (New Jersey, Pennsylvania, Virginia, and Delaware)... Read more

  • Oxford

    Tracing its roots to 1683, tiny Oxford remains secluded and untrammeled. Robert Morris, a merchant from Liverpool, lived here with his son, Robert Morris Jr., a signer of the Declaration of Independence... Read more

  • Queenstown

    The cove of Queenstown's harbor is protected by a bend of the mouth of the Chester River. Established in 1707 as "Queen Anne's Town," it became an important-enough port to be attacked by the British during... Read more

  • Rock Hall

    No longer just a side trip, Rock Hall, its hardy maritime character intact, has emerged as a viable destination in its own right, to be reached either by road or by boat. It reveres its heritage, despite... Read more

  • Salisbury

    Barges still ply the slow-moving Wicomico River between the Bay and Salisbury, the Eastern Shore's second-largest port after Baltimore. This urban center is a hub of commercial activity in the region and... Read more

  • Smith Island

    Chesapeake Bay's Smith Island has an intriguing heritage dating back more than three centuries. The residents are descendents of late-17th-century English settlers who made a living coaxing creatures from... Read more

  • Snow Hill

    The streets of Snow Hill, the Worcester County seat, are lined with huge sycamores and stately homes that reflect its days as a shipping center in the 18th and 19th centuries. Today's visitors are often... Read more

  • Stevensville

    Stevensville, just north of the Bay Bridge's eastern landfall, is a growing village of artists and craftspeople. Its galleries and studios sell original pottery, stained glass, and painted furniture as... Read more

  • St. Michaels

    St. Michaels, once a shipbuilding center, is today one of the region's premier leisure-time destinations. Its ever-growing popularity has resulted in more and more shops, cafés, waterfront restaurants... Read more

  • Tangier Island, Virginia

    Crab traps stacked 10 feet high, watermen's shanties on the water, and a landscape virtually devoid of modern commercialization characterize this Virginia island fishing community. Visitors love the unique... Read more

  • Tilghman Island

    A visit to Tilghman Island provides intriguing insight into the Eastern Shore's remarkable character. Leave your car and explore by bike or kayak. A handful of B&Bs and inns provide excellent accommodations... Read more