Maryland Crab & Oyster Trail: Upper Eastern Shore
Top of the Bay
Maryland Crab & Oyster Trail: Upper Eastern Shore
Top of the Bay
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. As you visit restaurants along the Crab & Oyster Trail be sure to look for the “True Blue” symbol to support Maryland’s local crab industry. Click here for a list of establishments certified as “True Blue.”
On the river banks, you’ll find quaint, friendly historic towns, like Havre de Grace, North East, Chesapeake 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, 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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On Kent Island, you’ll find yourself immersed in a bounty of seafood restaurants with spectacular water views, like Libbey’s Coastal Kitchen + Cocktails 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 and trails to explore. The Cross Island Trail and the Kent Island Trail 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.
Museums, Festivals, and Events
Discover the remarkable artistry and craftsmanship of traditional Maryland decoy carvers at the Havre de Grace Decoy Museum. Located on the banks of the Susquehanna Flats, the museum’s deck is a great spot to see migratory flocks of waterfowl over the Chesapeake Bay. Then explore the Havre de Grace Maritime Museum, where a working boat shop and environmental center are attractions that feature the history and ecology of the Bay.
In Rock Hall, check out the Rock Hall Watermen’s Museum to see tools of the watermen’s trade and learn about their lifestyle. A reproduction crab shanty house is a highlight. The Upper Bay Museum and C&D Canal Museum in North East and Chesapeake City are others waiting for you to explore.
Fall is a great time to visit the Upper Chesapeake: the crabs are fat, the weather is mild, the land and sky are painted with gorgeous colors, and wild oystering season has begun. Plus there are lively festivals with delicious seafood waiting for you. Come for
The Taste: Celebrating the Chesapeake in October at Chesapeake City to share the region’s seafood in a family-friendly atmosphere. The Rock Hall Fall Fest celebrates the start of the traditional oyster harvesting season and this tidewater town’s heritage. In November, head to The Great Havre de Grace Oyster Feast to find oysters cooked every way. You’re sure to find numerous tasty dishes you’ll love.
Trip Tips
The waters at the head of the bay have protected coves that can be calm and are a great place to try Stand Up Paddle-boarding. Take a lesson and launch from Kent Island Yacht Club and wind along marsh inlets to find solitude and connect with nature.
Travel through the town of North East to Elk Neck State Park for a wooded camping experience on a peninsula high above the Chesapeake Bay. Access the bay from Rogue’s Harbor on the Elk River. Swim in the North East River and hike to Turkey Point Lighthouse, which is perched on a 100-foot tall bluff at the head of the bay.
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.
