Maryland Crab & Oyster Trail: Upper Eastern Shore

Top of the Bay

Chesapeake City is ideally situated on Maryland’s upper Eastern Shore.

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Eastern Shore
Maryland's Upper Eastern Shore includes Cecil, Kent and Queen Anne's counties

Places along the way

Annie's Paramount Seafood & Steakhouse
500 Kent Narrows Way North
Grasonville, MD 21638

Bayard House
11 Bohemia Ave
Chesapeake City, MD 21915

Bay Shore Steam Pot
111 E Water St
Centreville, MD 21617

Bay Wolf Restaurant
21270 Rock Hall Ave
Rock Hall, MD 21661

Big Earls Seafood
1707 Main St
Chester, MD 21619

Billy's Crabs
1605 McGinnes Rd
Chestertown, MD 21620

Blue Bird Tavern
512 Washington Ave
Chestertown, MD 21620

Buck's Restaurant
314 East Main St
Rising Sun, MD 21911

Buddys Crabs
2756 Church Hill Rd
Centreville, MD 21617

Chesapeake Inn Restaurant & Marina
605 Second St
Chesapeake City, MD 21915

Chester River Seafood
4954 Ashley Rd
Rock Hall, MD 21661

Clark Seafood
23242 Handy Point Rd
Chestertown, MD 21620

Cranky Crab
6307 Main St
Queenstown, MD 21658

Fish Whistle at the Granary
100 George Street
Georgetown, MD 21930

Ford's Seafood & Restaurant
21459 Rock Hall Rd
Rock Hall, MD 21661

Fisherman's Crab Deck
3116 Main St
Grasonville, MD 21638

Fisherman's Inn
3116 Main St
Grasonville, MD 21638

Fisherman's Seafood Market
3032 Kent Narrow Way S
Grasonville, MD 21638

Harris Crab House and Seafood Restaurant
433 Kent Narrow Way North
Grasonville, MD 21638

Hemingway's at the Bay Bridge Marina
357 Pier 1 Rd
Stevensville, MD 21666

Hunters Crab & Seafood Market
4801 Main St
Grasonville, MD 21638

Kent Point Marina Seafood
107 Short Rd
Stevensville, MD 21666

Kentmorr Restaurant and Crabhouse
910 Kentmorr Rd
Stevensville, MD 21666

Knoxie's Table
180 Pier One Rd
Stevensville, MD 21666

Lee's Landing Dock Bar
600 Rowland Drive
Port Deposit, MD 21904

Mick's Crab House
902 E. Pulaski Hwy
Elkton, MD 21921

Mr. B's Seafood
114 State St
Stevensville, MD 21666

Nauti Goose Restaurant
200 W Cherry St
North East, MD 21901

O'Shucks Irish Pub
122 N Commerce Rd
Centreville, MD 21617

Osprey Point Restaurant
20786 Rock Hall Ave
Rock Hall, MD 21661

Passages Bar & Grill
20880 Rock Hall Ave
Rock Hall, MD 21661

Prime 225
225 Bohemia Ave
Chesapeake City, MD 21915

Schaefer's Canal House
208 Bank St
Chesapeake City, MD 21915

Steak & Main
107 S Main St
North East, MD 21901

Stevensville Crab Shack
116 Pier 1 Rd
Stevensville, MD 21666

Strongs Bay Seafood Inc
1723 Little Creek Rd
Chester, MD 21619

Tap Room Crab House
201 Bohemia Ave
Chesapeake City, MD 21915

The Jetty: Restaurant and Dock Bar
201 Wells Cove Rd
Grasonville, MD 21638

The Shanty Beach Bar
21085 Tolchester Beach Rd
Chestertown, MD 21620

The Wellwood Restaurant
523 Water St
Charlestown, MD 21914

Waterman's Crab House
21055 Sharp St
Rock Hall, MD 21661

Wellwood River Shack
523 Water St
Charlestown, MD 21914

Wesley's Restaurant
3700 Telegraph Road
Elkton, MD 21921

Woody's Crab House
29 South Main St
North East, MD 21901

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 Watermen’s Crab House in Rock Hall.

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Image Credit: Chester River Packet Company

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 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

Maryland serves up a diverse menu of seafood festivals, crab derbies and waterfront attractions. Explore maritime museums to discover what it was like to be a waterman in decades past. Try your hand at tonging or running a trotline, when you spend the day on a watermen’s heritage tour. See the unparalleled majestic beauty of a skipjack or log canoe race, both traditional watermen’s boats. Catch all the Chesapeake has to offer!

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See more of the Maryland Crab & Oyster Trail.

Image Credit: shardanasailingcharters-instagram

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.

Turkey Point Lighthouse at Elk Neck State Park in Northeast

Trails in this Region

Maryland Crab & Oyster Trail: Lower Eastern Shore
Chesapeake Wine Trail