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The Eastern Shore Travel Guide

  • Photo: (c) Jruffa |

Plan Your Eastern Shore Vacation

The eastern landfall of the Bay Bridge, which carries U.S. 50/301, is Kent Island, home to historic Stevensville and a small cluster of waterside restaurants, bars, lodging, art galleries, and several marinas surrounding the slim Kent Narrows channel. This

island gateway is 5.5 mi wide where U.S. 50/301 crosses it, and 14 mi long. William Claiborne established Maryland's first permanent settlement here in 1631 as part of Virginia.

Beyond Kent Island and its waning fishing towns, Queen Anne's stretches mostly northward as well as eastward to the Delaware line, its agricultural heritage readily apparent among burgeoning residential development, many designed as retirement communities.

Not unlike most of Maryland's Eastern Shore, Kent County is steeped in history and determined to preserve it. Its idyllic location between the Chester and Sassafras rivers is enhanced by a long, ragged Chesapeake Bay shoreline, many of its hidden hamlets untouched by time and savoring their quiet anonymity, while others struggle to balance their discovery by immigration from northern states with their heritage of 300 years.

In the summertime, both Kent and Cecil County are dotted with family-run farmstands. In addition to corn and tomatoes, locals grow cantaloupes, watermelon (including a yellow variety) peppers, squash, and many other fruits and vegetables—at a fraction of supermarket prices. Lockbriar Farms (410/778– has several locations in Kent County—call or go online for the harvest schedule and other information.

Cecil County includes the northern extremities of Chesapeake Bay. Its western boundary with Harford County, the Susquehanna River, is the Bay's principal northern tributary. Its southern boundary with Kent County is another tributary, the Sassafras River. The all-important Chesapeake and Delaware (C&D) Canal is cut between Cecil's third major river, the Elk, and the Delaware River, a major shipping route that connects Chesapeake Bay with Delaware Bay and the Atlantic Ocean. Its many acres of public parks and forests and well-known horse farms help preserve connections to the land.

One of the larger, yet more sparsely populated, counties on Maryland's Eastern Shore, Dorchester retains bits of early America in its picture-postcard towns and waterfront fishing villages. The expansive Choptank River, its northern boundary, and the rambling 28,000-acre Blackwater National Wildlife Refuge are idyllic locales for biking and boating, hiking and camping, and hunting, fishing, and crabbing.

Sailing the Chesapeake Bay nearly four centuries ago in search of new territory for his English king, Captain John Smith wrote that "heaven and earth never agreed better to frame a place for man's habitation." The eastern side of the Bay retains today its landscape of calm despite its proximity to Baltimore and Washington, D.C.

An early-American aura pervades most of the Eastern Shore. The peninsula is rich with maritime heritage (you will see many boats!), and the area's architecture reflects its colonial and pre-colonial history (view the stately homes in Chestertown and Oxford). The Eastern Shore's first permanent English settlement—indeed the first in Maryland and one of the earliest along the Atlantic—took root on Kent Island, now Queen Anne's County, in 1631. Many Eastern Shore families have been here for generations; residents of Smith Island still speak with an Elizabethan lilt.

A visit to the Eastern Shore might consist of exploring historic sites, strolling through wildlife parks and refuges, pausing at a few of the myriad shops, dining at third-generation-owned waterfront restaurants, and overnighting at inns and bed-and-breakfasts in one of the region's enchanting communities. It you prefer the ocean to the bay, a different experience all together awaits at the popular summertime destination of Ocean City. Clinging to a narrow barrier island off the southeastern edge of Maryland's Eastern Shore, Ocean City has high-rise condos, a boardwalk, multiple restaurants and bars, and theme park-like attractions. The bustling, ocean-side culture differs dramatically from that of the Chesapeake.

The three counties of Maryland's Lower Eastern Shore—Wicomico, Worcester, and Somerset—contain the contrasting cultures of the Chesapeake Bay and the Atlantic coast but still share a common history.

The Nanticoke River flows out of southern Delaware across fertile farmland between Dorchester and Wicomico counties into the Chesapeake Bay's Tangier Sound near the Blackwater National Wildlife Refuge. To the east the Atlantic alternately caresses and pounds Worcester County's sturdy shorelines and fragile barrier islands stretching from the Delaware Bay to easternmost Virginia. Somerset County, comprising the Eastern Shore's southeastern corner, includes a few communities clinging to the shoreline of Tangier Sound among sprawling Wildlife Management Areas and an island State Park.

The Main Street shops, early-American inns, and unsung restaurants of the small towns in this region seem a century removed from the boutiques and galleries, high-rise hotels and condos, myriad eateries, and nightlife of nearby Ocean City.

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Top Reasons To Go

  1. Sail on a Historic Skipjack Though they once dominated the Chesapeake Bay waterways, these traditional fishing vessels are now nearly extinct—but you can hop aboard one of the few remaining ones and experience a bit of history.
  2. Crack into Maryland's Trademark Crustacean Don't leave the Eastern Shore without sampling the slightly sweet taste of the Chesapeake renowned blue crab at a down-home eatery, cracking shells with your own wooden mallet.
  3. Get Back to Nature Bike the Blackwater National Wildlife Refuge or paddle the tidal marsh pathways of the Fishing Bay Water Trail and look for bald eagles.
  4. Be Touristy in Ocean City Maryland's barrier island has year-round leisure-time opportunities—mid-summer for 24/7 activity and unparalleled people-watching, mid-winter for bracing coastal solitude, or idyllic moments in the months in between.

When To Go

When to Go to Maryland's Eastern Shore

Traditional summertime months, i.e. school vacation time, are the busiest throughout the region. Ocean City attracts not only visitors for weeks-l...

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