Upper Eastern Shore Crab and Oyster Trail

Top of the Bay

Waterman’s Crab House Restaurant and Dock Bar is ideally situated on Maryland’s upper Eastern Shore.

Photo By: Clark Vandergrift

Places along the way

The water-laced landscapes 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 food 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, Watermen’s Crab House in Rock Hall, or the best kept secret - Price’s Seafood in Havre de Grace.

Sail aboard the historic Schooner Sultana, based in Chestertown. The two-hour sails are a great way to learn about the Chesapeake Bay ecology. Passengers are encouraged to help raise the sails, steer the ship and explore the authentically reproduced crew’s quarters below-decks.

Photo By: Clark Vandergrift

On Kent Island, you’ll find yourself immersed in a bounty of seafood restaurants with spectacular water views, like Hemingway’s and The Narrows. Take your time and explore the island, which is at the eastern end of the Chesapeake Bay Bridge and boasts a half dozen marinas. If you get off the beaten path, you’ll find sandy beaches to explore and trails that traverse wetlands, surrounding you with tall grasses, the stately and towering loblolly pines and stunning bay scenery.

The pace of living seems to slow on the Upper Eastern Shore, rejuvenating the weariest of souls. For the perfect ending to your fun-packed day, soak up a peaceful crimson sunset reflecting over the water while on a chartered sailing excursion out of Rock Hall – then sail by the light of the moon.

Photo By: Clark Vandergrift

Maryland Lore

A commercial crabber will typically set 50 to 200 crab pots a day. A crab pot is a square trap, which is baited and thrown into the water. The pot is attached to a rope that is then attached to a buoy or dock. The crabs are harvested every day or two.

Trails in this Region

Central Maryland Crab & Oyster Trail
Lower Eastern Shore Crab and Oyster Trail