Journey to the Water’s Edge—Talbot County and the Eastern Shore of Maryland

Sunset over the Chesapeake Bay off Tilghman Island in Talbot County, Maryland

This spring, plan your escape to Michener’s Chesapeake with a weekend in Talbot County, Maryland. One iconic town in this gorgeous county is my personal favorite, Tilghman Island, Maryland on the pristine shores of the Choptank River. Tilghman Island is a scenic 20 minute drive from St. Michaels, and remains a true working waterman’s village with excellent fishing and fresh seafood. The original skipjacks, the first commercial sailing fleet in North American, are on display at Dogwood Harbor. 

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At Tilghman Island you’re sure to enjoy watching the seabirds like the Great Blue Heron and Ibis.

For very reasonable rates you can stay at a family guesthouse or one of the charming Bed & Breakfasts style inns. Romance seekers might enjoy the secluded Black Walnut Point Inn, nestled in acres of pine woods and marshes, and surrounded on three sides by the Chesapeake Bay. Walking along the grounds of this private resort feels like the only inhabitants sharing your space are the great blue herons and the wild eagles.

Talbot County Chesapeake Bay

The most prominent feature of Talbot County’s waterfront are the historic marinas where you’ll occasionally see a working watermen come in with their catch.

Wylder Hotel Tilghman Island is a charming hotel located on 9 acres of Chesapeake Bay waterfront. If you want luxury and elegance, there are close-by resorts which offer an abundance of fine dining, sports and entertainment. Check out Inn at Perry Cabin or St Michaels Harbour Inn, resorts situated on the water catering to the couple or family who seeks first class service and accommodations.

Beginning anglers can join a private fishing charter or if it’s warm enough, rent a kayak or jet ski at Knapp’s Narrows Marina and Inn to tool around the extensive shoreline. 

After a day of wind and spray, your appetite will be whetted for fresh seafood caught by the local fisherman. Two if By Sea is a diner featuring Cajun cooking and locally grown produce like fresh corn and tomatoes.  They also offer their “Down Home Country Cooking Classes” if you want to learn how to make MidAtlantic cuisine. Or for waterfront, outdoor dining, try Marker 5 Restaurant & Tiki Bar.

St Michaels Maritime Museum in Talbot County
The Maritime Museum in St Michaels in Talbot County

Do not miss the chic town of St. Michaels; there are at least a dozen adorable boutiques and the Chesapeake Bay Maritime Museum that are worth a look. Rent a bike for the 15 mile ride between Tilghman Island to St. Michael’s, then quench your hunger with lunch on the water at one of the cafes along the shoreline. The roads are maintained for bikers and the local authorities work to protect the safety of the route. The trails are completely flat and very scenic. Nature lovers can tour the Pickering Audubon Sanctuary in nearby Easton, take a catamaran ride, or test the products at the St. Michael’s Winery

The Harbor at St. Michaels in Talbot County MD
St Michaels waterfront features Hooper Strait Lighthouse which allows visitors to climb inside to learn how they operated in 1867.

To head to Tilghman, drive east on Route 50 to the Bay Bridge. After you pass over this three mile expanse, you immediately begin to feel the calm settle over you as you absorb the pace and hospitality of these water towns of the Eastern Shore. Continue through farmland and tobacco fields past the driveways of antebellum mansions with names like the Wild Goose Perch.

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The view of the St. Michaels’ harbor from the Inn at Perry Cabin

Some landmarks along the way, like the Old Mill at Wye Oak State Park provide historical context to the region. Continue to make your way to the Bay again heading toward Easton, worth another brief stop if you want to pick up some picnicking supplies for your day on the water. Take Route 322 through St. Michaels, and then further East until the land stops. At Tilghman you’ve arrived in what is still an authentic, unspoiled town on the Chesapeake Bay.

Learn how the Wye Grist Mill & Museum processes wheat to make delicious flour, a process that has continued here since 1682. You can buy flour to take home!

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Freelance writer and photographer specializing in vivid, deeply reported stories about food, travel and family.

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