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.

Let it unfold.

Not everything needs to be scheduled to be meaningful.

Allen

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Cities to Explore

Stay a little longer.

Rushing through a place rarely does it justice.

Berlin

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Follow what feels interesting.

Curiosity is usually a better guide than a strict plan.

Bethlehem

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A place to slow down.

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

Bishops Head

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Let the road decide.

Plans are useful, but flexibility is where the real discoveries happen.

Barclay

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Stay a little longer.

Rushing through a place rarely does it justice.

Bishop

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Go where you feel alive.

Pay attention to the places that pull you in without explanation.

Betterton

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The road is the experience.

Getting there is often the point, not just the outcome.

Bishophead

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Take the detour.

The extra miles are often where the story begins.

Bainbridge

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Explore a County Caroline County 11 cities  ·  9 counties in Eastern Shore Browse all counties →
Explore a City Berlin 19 attractions  ·  140 cities in Eastern Shore Browse all cities →