Eastern Shore

The Eastern Shore covers the Maryland portion of the Delmarva Peninsula, the broad agricultural-and-water country east of Chesapeake Bay running from the Pennsylvania line south to the Virginia border. The terrain is flat coastal plain — pine flatwoods, salt marsh, tidal creeks, and farmland — drained by the Choptank, Nanticoke, Pocomoke, and Wicomico rivers as they work west into the Bay. The Atlantic shore on the eastern edge holds Maryland’s only ocean beach at Ocean City and Assateague. Nine counties cover the region. Worcester holds Ocean City, Berlin, and Snow Hill; Wicomico holds Salisbury (the largest city); Talbot holds Easton, St. Michaels, and Tilghman Island; Dorchester holds Cambridge; Queen Anne’s holds Stevensville on Kent Island; Kent holds Chestertown; Caroline holds Denton; Cecil holds Elkton. Assateague Island National Seashore (with the wild ponies) and the Blackwater National Wildlife Refuge handle the major public lands; the Harriet Tubman Underground Railroad National Historical Park sits in Dorchester. Most trips here split among three threads. Ocean City pulls the boardwalk-and-beach summer crowd; the Bay-side towns of St. Michaels, Easton, and Cambridge run quieter sailing-and-oyster-bar weekends; Tubman, Frederick Douglass (born in Talbot County), and the Underground Railroad sites carry the historical itinerary.

Start early. Stay late.

The edges of the day tend to hold the best experiences.

Bainbridge

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Cities to Explore

Take the detour.

The extra miles are often where the story begins.

Allen

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Keep it easy.

The best days usually come without pressure or overplanning.

Bishophead

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Let it unfold.

Not everything needs to be scheduled to be meaningful.

Betterton

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Worth the stop.

Some places don't need much time, just the right moment.

Bishop

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Not every place needs a reason.

Sometimes it's enough just to be there.

Bishops Head

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Start early. Stay late.

The edges of the day tend to hold the best experiences.

Barclay

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A place to slow down.

Not every stop needs to be busy to be worth your time.

Berlin

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Keep it easy.

The best days usually come without pressure or overplanning.

Bethlehem

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Explore a County Caroline County 11 cities  ·  9 counties in Eastern Shore Browse all counties →
Explore a City Allen 0 attractions  ·  140 cities in Eastern Shore Browse all cities →