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Eastern Shore (Maryland)

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Eastern Shore (Maryland)

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Tidal wetlands on the Eastern Shore

The Eastern Shore region is Maryland's part of the Delmarva Peninsula, which is shared with Delaware and Virginia's Eastern Shore. The area is rich in culture and history, making it a great travel destination for anyone who's looking to soak up the local culture!


  • Cambridge — a historic town of 10,000 by the Bay Bridge, one-time home to Harriett Tubman, and even Annie Oakley.
  • Chestertown — small historic town on the Chester River.
  • 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.
  • St. Michaels — pretty, historic small town, with nice boutique shopping.
  • Salisbury — the largest city in the region.
  • Snow Hill — historic small town on the Pocomoke River.

Other destinations

  • Assateague Island National Seashore — 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 communties 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.


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 Virginia, with which it shares a border, as opposed to the western portion of Maryland, which is perceived by locals as more liberal. For this reason, many residents take offense being compared to Marylanders from the "Western Shore" or other side of 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 recently in 1998 for the Eastern Shore becoming its own state. Because of its unique location, Maryland's different regions portray different regional characteristics. For tourists coming from the South, be aware that many, if not most, residents of the Eastern Shore consider themselves Southerners. The Eastern Shore has a long history related to the rest of the South and many residents have ancestors that fought for the Confederacy in the Civil War, or the "War of Northern Aggression" as it is called in the area. Consequently, attempts to dissuade residents otherwise may be met with a heated response.


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.


Its location on the Atlantic Coastal Plain in Maryland gives the Eastern Shore a humid subtropical climate, with hot, humid summers and cool to mild winters. For botanists, the USDA hardiness rating is a 7B-8.


The Eastern Shore, because of its proximity to Virginia and historic isolation from the Western Shore, maintains a Southern accent akin to the Tidewater region of Virginia. This is especially true of the four counties on the "Lower Shore" or counties nearest Virgina: Wicomico, Dorchester, Somerset, and Worcester. In addition, are interesting dialects to be found in the isolated island communities of the Chesapeake Bay, where Victoria-era British accents have been near-perfectly preserved.

Get in

By car

US-50 and US-13 are the main roads into the Eastern Shore, with US-50 leading from Annapolis and the rest of Maryland, US-13 leading north south from Eastern Virginia to Delaware. US-301 is the most useful road for the seldom-visited northern parts of the region.

By plane

The nearest big airports are in the D.C.-Baltimore metropolitan region: Dulles International, Reagan National, and Baltimore-Washington International. From any of the above, you will want to rent a car.

Get around

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.


The Chesapeake Bay is likely the main attraction on the Eastern Shore. It is rich with activities, watermen culture, great seafood, and is simply beautiful. To learn more about Chesapeake culture, there are a number of good museums around the region, such as the J. Millard Tawes Historical Museum and seafood processing plant tour in Crisfield and the the Maritime Museum of St. Michaels. Smith Island is another great stop for Chesapeake watermen culture, where you'll find accents dating back to Victorian England, and a local sense of place and purpose inseparable from the Bay and its sea harvests. Hooper's Island is a bit less exotic than Smith Island, but still a great off-the-beaten-path locale for natural beauty and the historic Phillips Seafood Factory. The ever-popular resort town of Ocean City, in addition to the beach and boardwalk, has a couple offbeat museums, most notably the Ripley's Believe it or Not Museum. It is also right next door to the gorgeous barrier island of Assateague Island National Seashore. Assateague, with its natural beauty and wild ponies strolling the long, quiet, white sand beach, is not to be missed. Other picturesque tourist destinations include the small historic towns around the region, particularly south of US-50. The town of St. Michaels on a neck surrounded by water, the colonial former port of Oxford, Chestertown, Stevensville on Kent Island, and Snow Hill are all great options for lazy strolls and historical sightseeing.



Wetlands on Assateague Island

The Eastern Shore is rich with wild areas, most famously Assateague Island National Seashore and State Park, but also less known state parks, forests, and wildlife preserves. Look for deserted beaches on Janes Island State Park by Crisfield and kayaking/canoeing in Pocomoke River State Forest by Snow Hill. Ocean City has long been popular with Baltimoreans and Marylanders from the Western Shore in general, thus rendering the flavor of Ocean City life unlike that of the rest of the Shore. The skyline, featuring many tall hotels and condominiums, is also a stark contrast to the rest of Delmarva. On the southern end of Ocean City is a highly popular recreational boardwalk spanning over thirty blocks and featuring carnival rides and games, restaurants, bars, arcades, and clothing boutiques.


The Eastern Shore is not a big metropolitan shopping corridor—visitors from the rest of the state consider it quite the reprieve from that sort of thing! Nonetheless, there is the big Centre at Salisbury—a large mall with Macy's and many other stores. Other local shopping is mostly limited to small, but charming, boutiques and quiet souvenir shops in the smaller historic towns that see significant tourism. Since the boom times of the year are during the warm months, many of these shops will be closed in the winter. St. Michaels is considered the regional center of this type of small town boutique shopping.


No trip to the Eastern Shore would be complete without having sampled the region's world-famous Blue Crabs and 7-layer Smith Island Cake. Many restaurants in the area serve crab, crab cakes, and Chicken Chesapeake (Chicken with Crab Imperial).


Nightlife is largely absent from the Eastern Shore, with the one very glaring exception of Ocean City, which is full of nightclubs, bars, and the like, which operate even in the slower winter season.


Hotels outside Ocean City are going to be cheap to mid-range, bland chains. For more local character and charm, however, do as the Maryland and D.C. visitors do, and opt instead for any of the beautiful, historic bed & breakfasts around the countryside and the small towns, where you will really get to meet locals, and relax in a pretty setting.

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. Jellyfish live in the Chesapeake Bay during warm-weather season, and can be a hazard to swimmers.

Get out

  • 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 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.
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