Eastern Shore (Maryland)

• 🌍 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.

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.

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 Virginia: Wicomico, Dorchester, Somerset, and Worcester. In addition, are interesting dialects to be found in the isolated island communities of the Chesapeake Bay, particularly, Smith Island, where pseudo Elizabethan-era English accents have been preserved.

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 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 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.

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 across the bridge 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.

Waterfowl Festival is an annual wildlife arts and sportman's expo located in Easton. It draws tourists from all over the U.S. and the world and usually falls on the second weekend of November.

Like the Western Shore, the Eastern Shore has a lively sailing and boating culture.

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 Boscov'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. 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). Crab cakes, soft-shell crab sandwiches (for the strong-stomached), cream of crab soup, and of course good old steamed crabs served with Old Bay may be the area's most famous dishes, but the other seafood is quite tasty as well.

Nightlife like you'll see in urban areas 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. However, smaller towns often have a bar or two, even if they're not the happening places Ocean City bars are.

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.

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.

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.

• 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.