Maryland Crab & Oyster Trail: Upper Eastern Shore

Top of the Bay

The water-laced landscapes of Maryland's upper Eastern Shore at the head of the bay, are the perfect place to paddle, sail or ply your way through the wide, lazy rivers that saunter toward the Chesapeake. Pack your crabbing and fishing gear or hire a charter service to escort you. The mighty Susquehanna and the Sassafrass and Chester rivers provide ample nautical miles of adventure. Guides and outfitters are at the ready to get you out on the water.

On the river banks, you’ll find quaint, friendly historic towns, like Havre de Grace, North EastChesapeake City, Chestertown and Rock Hall waiting for you to explore. They offer everything from five-star restaurants with signature dishes and creative cuisine, to fun waterside establishments with an island vibe, like Schaefer’s Canal House and The Jetty, to local hangouts that have developed their own culinary expressions.

For upscale fine dining, try the Bayard House in Chesapeake City, Osprey Point Inn in Rock Hall or Rustico Restaurant and Wine Bar in Stevensville, and there are many more. To sample the flavor of local culture, check out Woody’s Crab House in North East, or Waterman’s Crab House in Rock Hall.

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