Eastern Shore

Understand

The Eastern Shore was largely isolated from the rest of Maryland until the construction of the Chesapeake Bay Bridge in 1952. As a result, values tend to be conservative and closely related to the rural South, as opposed to mainland Maryland or Virginia, which is perceived by locals as more liberal. For this reason, many residents take offense being compared to Marylanders from across the Chesapeake Bay Bridge. This sense of alienation from the rest of Maryland has spurred several attempts to split off from the state of Maryland. Proposals have been debated in the Maryland General Assembly in 1833-1835, 1852 and in 1998 for the Eastern Shore becoming its own state. Because of its unique location, Maryland's regions portray different regional characteristics.

Many, if not most, residents of the Eastern Shore consider themselves Southerners. Maryland was a border state during the Civil War. By 1860 49.1% of the African Americans in the state were free.

Geography

The Eastern Shore is part of the Delmarva Peninsula. The topography of the Eastern Shore is flat. Mountains are non-existent and hills are rare. Because of its proximity to the Chesapeake, the Eastern Shore has several islands, marshes, beaches, and inlets.

Climate

See Delmarva Peninsula#Climate

Cities

West of Delaware

• Bethlehem (called "Bethlem" by locals)
• Cambridge — a historic town of 10,000 by the Bay Bridge, one-time home to Harriet Tubman, and Annie Oakley.
• Chesapeake City — a town on the Chesapeake and Delaware Canal.
• Chestertown — small historic town on the Chester River.
• Denton
• Easton — another historic town near the birthplace of Frederick Douglass.
• Oxford — a historic, small, waterfront town.
• Preston
• Rock Hall – a charming small town on the Bay, popular with boaters
• St. Michaels — pretty, historic small town, with nice boutique shopping.

South of Delaware

• Crisfield — historic, but gritty port town—the one-time seafood capital of the East Coast.
• Ocean City — the popular beachside resort town, known best for its boardwalk and nightlife.
• Princess Anne — historic small town and county seat.
• Salisbury — the largest city in the region.
• Worcester County — several historic small towns

Other destinations

• Assateague Island — a true gem of the East Coast shoreline; a barrier island with a beautiful beach, wild ponies, and nature trails through the bayside wetlands.
• Chesapeake Bay — the Great Shellfish Bay, and the source of Maryland's maritime and seafood culture.
• Hooper's Island — a quiet collection of three tiny islands home to fishing communities and the historic Hooper's Island Lighthouse.
• Kent Island — a pretty island off the Bay Bridge, home to historic Stevensville.
• Smith Island — a watermen island long lost in time, with nary a car to its name.
• Harriet Tubman Underground Railroad Visitor Center – the visitor center is 1 of 36 stops on the Harriet Tubman Underground Railroad Byway (a 125-mile, self-guided historical tour by car with 36 sites that chronicles Harriet Tubman's search for freedom from slavery). The visitor center is open 7 days a week with free admission and contains exhibits, library, theater and gift shop.

Get in

By car

US-50 and US-13 are the main roads into the Eastern Shore, with US-50 leading across the Bay Bridge from Annapolis and the rest of Maryland, US-13 leading north south from Eastern Virginia to Delaware. US-40 also provides entry from Cecil County in the North via an entry to MD-213 in Elkton. US-301 is the most useful road for the seldom-visited northern parts of the region.

By plane

The nearest major airports are: Washington Dulles International Airport (IAD), Reagan National Airport (DCA), Baltimore-Washington International Airport (BWI), and Salisbury-Ocean City Wicomico County Airport (SBY).

SBY is in Salisbury, MD which is about a 27-mile drive from Ocean City by way of US-50. While SBY is not a big airport, it is included on this list because it is the only somewhat big airport on the Eastern Shore of Maryland. The only airline that flies into SBY is American Airlines. There is an onsite Enterprise Rent-A-Car location at SBY and other transportation options include: Coast to Coast Limousine Inc, Gene's Limousine Service Inc, Gene's Taxi Co, Yellow Cab, Bailey's Taxi Services, Salisbury Taxi Co, and other taxi services.

BWI, DCA, and IAD are all in the D.C.-Baltimore metropolitan region which is on the other side of the Chesapeake Bay. Most major airlines fly into these airports and many car rental agencies have locations at these airports. There are also many taxi and limousine companies and bus services in the D.C.-Baltimore metropolitan region.

The BayRunner shuttle is the airport shuttle services for BWI. The Eastern Shore pick up/drop off locations are: Ocean City, Ocean Pines, Salisbury (not at airport), Cambridge, and Easton. Greyhound also has several stops on the Eastern Shore and an onsite location at BWI.

If you are traveling to one of the more northern parts of the Eastern Shore, it will be closer to fly into Philadelphia International Airport (PHL). SBY is the closest airport for the southern parts of the Eastern shore. If you wish to fly into a larger airport, then Newport News/Williamsburg International Airport (PHF), Norfolk International Airport (ORF), and Richmond International Airport (RIC) all might be closer than BWI, DCA, and IAD depending on your destination.

Most major airlines fly into PHL, ORF, and RIC.

The airlines that fly into PHF are American and Delta.

By train

Amtrak's nearest train stations are: Baltimore- Thurgood Marshall Airport (BWI), Baltimore- Penn Station (BAL), Newark, DE (NRK), Wilmington, DE (WIL), Richmond- Main Street Station (RVM), Richmond-Staples Mill Rd (RVR), Williamsburg, VA (WBG), Newport News, VA (NPN), Washington, D.C.- Union Station (WAS), North Philadelphia (PHN), and Philadelphia-30th Street Station (PHL). From these train stations you can take a bus to various cities on the Eastern Shore.

By boat

As of June 2026, there are no regular commercial ferries crossing the Chesapeake Bay, though there are some in the planning stages. However, most waterfront towns have marinas where privately owned boats can park freely.

By foot

The Appalachian Trail goes from Maine to Georgia and 41 miles of the trail are in Maryland and the Chesapeake & Ohio Canal National Historic Park rails to trails route stretches from DC to Columbia. Once you've walked in Maryland follow google maps walking directions to you're desired Eastern Shore location.

Get around

By bus

Shore Transit System has over 200 stops in the tri-state area. Greyhound has a few Eastern Shore stops.

By car

Unless you prefer to stick to the water when traveling, a car is an absolute necessity to have a good time on the Eastern Shore. The aforementioned routes are also the principal roads around the region, especially US-50.

By boat

Ferries are available from Crisfield to Deal Island, Smith Island, and Tangier Island. Marina's are quite easy to come by for travelers with their own boat! The Chesapeake Bay's fingers extend towards virtually any town, save those right by the Atlantic beaches, so a private boat will really get you to just about all the small historic towns and nature reserves dotting the landscape.

By bike

The region's relatively flat landscape lends itself well to bikers. There are multiple bike shops, and there's no shortage of scenic bicycle trails.

Stay safe

Poison ivy is widespread along forest edges. It shouldn't prevent you from enjoying nature, but learn to recognize it before you go off-trail. Ticks, mosquitoes and chiggers abound during summer months. Humidity can be quite high during the summer, so stay well hydrated. The Copperhead, a poisonous snake, is found in some areas, though less commonly than in the hills and mountains across the Bay. Jellyfish live in the Chesapeake Bay during warm-weather season, and can be a hazard to swimmers.

The county's vast areas of agricultural land provide a perfect habitat for whitetail deer, which are often involved in car accidents. Be vigilant on the road, especially at night, at dawn and dusk, and in the breeding season from October to January. Visitors should also be aware of possible impaired drivers, especially on the holidays and weekends.

Crime is generally not an issue for visitors to the Eastern Shore, but it's wise to watch your belongings closely if you visit the Ocean City area during spring break and summer weekends, when the area sees hundreds of thousands of vacationers, including many young people. The same applies to Salisbury and Cambridge; crime rates tend to be a little high but visitors are unlikely to find trouble if they watch their surroundings.

Go next

• Just to the south in Eastern Virginia are Chincoteague and Tangier Islands. The former is known for its beauty and wild ponies (similar to Assateague, but with houses and rental possibilities), and the latter is the twin of Smith Island, with the same time-stopped-in-the-eighteenth-century culture.
• Just north of Ocean City are the perhaps even more popular beaches of Delaware at Rehoboth and Bethany.
• If you're looking for more Chesapeake culture, look to the west in Annapolis, or to the southwest in the small historic towns of Southern Maryland. The latter is a bit hard to reach by car, but a very manageable boat ride. Or even look north to a very different culture, but one still firmly tied to the Bay, in the big port city of Baltimore.