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Talbot County

Across the Choptank River, Talbot shares its southern waterfront border with Dorchester County. Offering an authentic Eastern Shore lifestyle in several distinct communities, Talbot’s five towns and 600 miles of waterfront are a magnet for families and retirees.


Home to the celebrated Waterfowl Festival, Easton has excellent shops, plentiful parks and a lively arts scene. Considered Talbot’s “big city,” this historic town is also the county seat. Residents enjoy concerts at the Avalon Theater, exhibitions at the Academy Art Museum, and world-class cultural events.

The downtown and surrounding residential neighborhoods feature a mix of clapboard cottages, stately Victorian, Georgian or Federal-style homes, and newer construction in communities of Easton Village, Cook’s Hope, Easton Club and Easton Club East for 55+.


One of the oldest towns in Maryland – and one of the prettiest – this 17th-century seaport is steeped in history. With Town Creek to the east and Tred Avon River to the north and west, Oxford’s waterways teem with yachts, workboats and small craft. The town is home to the Oxford-Bellevue Ferry, the oldest privately operated service in continuous use. Author James Michener penned the novel Chesapeake at the still-operating Robert Morris Inn.

Homes in the historic district feature traditional architectural styles of the 18th, 19th, and 20th centuries. Stately manors and working farms are primarily found along waterfront estates outside of town. Oxford boasts a beautiful waterfront park, eclectic restaurants and the popular Highland Creamery.

St. Michaels

Situated along the Miles River, St. Michaels’ picturesque setting is favored by Hollywood producers who made it the backdrop for Wedding Crashers and Clara’s Heart. Known as the town that fooled the British during the War of 1812, residents hung lanterns in trees outside limits to trick the attacking army by providing a false target.

Today, St. Michaels is home to the Chesapeake Bay Maritime Museum, Harbourtowne Resort and the Inn at Perry Cabin by Belmond. With two-dozen restaurants, St. Michaels is a regional dining destination. From contemporary and classic waterfront estates to Federal and Revival style architecture in town, St. Michaels – and nearby communities of Royal Oak and Newcomb – offer a variety of housing styles including tidewater colonials and cottages.

Tilghman Island

A quintessential waterfront village, Tilghman Island sits on the southernmost tip of Talbot County. Cushioned between the Chesapeake Bay and the Choptank River, the pristine waterfront provides a peaceful quality of life. Accessible by a drawbridge, Tilghman has several marinas offering charter cruises.

Known for sport fishing, fresh seafood, and the center of Talbot’s watermen community, Tilghman businesses, attractions (Phillips Wharf Environmental Center), and events celebrate their distinct culture. Here you’ll find classic homes including traditional Eastern Shore styling to stunning contemporaries and everything in between.


Trappe is a farming community with waterfront homes along the Choptank River’s creeks and tributaries. With easy access to Ocean Gateway (Route 50), Trappe is 10 minutes from Downtown Cambridge and equidistant from Easton.

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