Visit Us

Experience a diverse and exciting part of Maryland’s Eastern Shore. Meet the people who live here, enjoy the landscapes and towns they treasure, and share the best of their traditions, arts, and foods. Explore charming shops or stay overnight in a country inn or quaint B&B. The spectacular stories of the small towns and four counties that make up this special region… Caroline, Kent, Queen Anne’s and Talbot Counties… are just waiting to be told.

History of the Bay | Working the Land | Working the Water | Enjoy our Small Towns | Food for the Soul
A Spectacular, Fascinating Natural Landscape | African American Heritage | Trails and Byways

History of the Bay…

Residents here, past and present, have selectively embraced change in response to the particular resources and geography of the Chesapeake Bay, and in the process have themselves changed this place.

Humans have lived beside the Chesapeake Bay since it began.  As the waters of the Bay have risen in the millennia following the end of the last Ice Age, prehistoric settlers learned to exploit the rich resources of the well-watered landscape and mild climate.  Known (and protected) American Indian sites range from rare “archaic” sites, such as the 13,000 year-old Paw Paw Cove site on Tilghman Island, to “contact” sites where Captain John Smith and other Europeans first visited the indigenous tribes of the Eastern Shore.

Visitors can view a replica of Smith’s small vessel, more than four hundred years since Smith’s legendary journeys around the Chesapeake Bay in 1608.  Colonial archaeological sites abound, providing insights to the major changes wrought to the land and the Bay beginning with European settlement. But the story doesn’t end there, as residents here work to adapt their modern lives to the ecological needs of the Chesapeake Bay and its living resources.  Visitors can learn about the most up-to-date science and methods of “living lightly” on the land.

 History of the Bay – Sites to Visit

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Working the Land…

This part of Maryland’s Eastern Shore is known to historians as the Breadbasket of the American Revolution.  Still a wealthy and scenic grain growing area, it is one of the oldest remaining working landscapes in North America, the largest single area of agricultural lands left on the Atlantic Coast.  It is also one of the most protected landscapes outside the American West, thanks in large part to local and state efforts to protect farmland.

Early conversion to wheat from tobacco in the 18th century proved to be a particularly successful move.  Wheat allowed farmers to diversify away from the boom and bust of tobacco and prosper from crop failures in Europe, emancipating slaves whose labor was no longer needed once intensive tobacco cultivation was abandoned.  The rich colonial towns of the Eastern Shore relied in part on the wealth from the region’s plantations, and the many millers of the region grew wealthy grinding flour to ship to the West Indies.

Working the Land – Sites to Visit (links)

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Working the Water…

The evolution of the Chesapeake Bay clipper-schooner ship in the 18th century ranks among the most important events in the history of naval architecture, a worldwide influence on global trade.  It was the most visible of a host of Bay-built watercraft constructed in this region.  Both traditional and new, designs of boats here respond to both the demands of the Bay and the needs of shippers and watermen.

Although the rich seafoods of the Chesapeake Bay were hardly an economic resource in the Colonial era, by the end of the 19th century the lowly oyster, the food of choice for the newly rich of the Roaring Nineties, had transformed the region’s economy.

The skipjack evolved at the end of the Age of Sail, crowding a huge sail, to capture the forgiving winds of the Bay, onto a wide, shallow-bottomed hull ideal for sailing over shallow oyster bars with mechanized dredges.  The swift three-masted log canoe unique to this region – still seen at several spectacular regattas held each year – evolved to rush the day’s catch to Baltimore.  Ironically, however, what stimulated the seafood
industry that arose after the Civil War were modern technologies, especially canning, refrigeration and railroads.  Today’s skipjack fleet, the last commercial sailing fleet in the United States, finds most of its berths in the Stories of the Chesapeake Heritage Area.

Working the Water – Sites to Visit

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Enjoy Our Small Towns…

Tour the small towns, none larger than 15,000 in population, and the even smaller villages that dot the Stories of the Chesapeake Heritage Area.  Stop at country stores, take a break by boat landings, walk along the tree-lined streets of front porch neighborhoods, visit quiet country cemeteries and one-room schoolhouses.  Walkable, parkable – experience the unique qualities of small town life, the way “smart growth” aims to be.

The region’s employment diversified in response to the opportunities offered by the region’s unique natural resources and geographic advantages.  Shipping, boatbuilding, fishing, hunting, milling, ironmaking, canning and trade stimulated the growth of such places as Federalsburg, Oxford , Millington, Rock Hall, Galena, and Betterton.

, Chestertown, Denton and Easton benefitted additionally from their status as county seats, each with a beautiful early courthouse.

Free black communities existed as early as the 17th century.  Unionville grew up immediately after the Civil War on land donated by its Quaker owner to his former slaves, returning Civil War veterans.

Watermen’s villages, such as Grasonville and Kent Narrows (Chester) grew up along every accessible harbor or landing. Rock Hall prospered as a fishing location and as one end of a ferry crossing that took travels to and from Annapolis and Philadelphia. Church Hill and Wye Mills are examples of colonial era villages that grew up first around a mill, and then a church positioned along the road that crossed the mill dam.

Rosenwald schools, large and small – built in the 1920’s from grants provided by Julius Rosenwald, founder of the Sears, Roebuck fortune, to black communities who could raise matching funds – still stand in a number of locations, highlights of a large collection of early schools.  Three early theaters still survive in Chestertown , Church Hill and Easton, with a fourth unique performance space, The Mainstay , occupying a storefront in Rock Hall.

Additional Links

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Food for the Soul

The colonial history of the Stories of the Chesapeake Heritage Area is closely interwoven with the unusual story of an early religious pluralism.  Religious worship encompassed not only the Catholic faith of the Maryland colony’s founder, Lord Baltimore, but also Anglican, Quaker, the Methodist denominations – and in the early 19th century, the African Methodist Episcopal (AME) Church, whose seventh bishop was born in the region in 1836.  The remarkable population of churches here includes several that are nationally significant, as well as numerous 19th century country crossroads chapels that mark this landscape as “the Garden of Methodism.”  Religious leader here called for abolition of slavery in the 18th century.  The Underground Railroad, the invisible conduit for escaping slaves that arose in the early 19th century, grew here with the help of Quakers, black mariners, and a remote landscape next to Delaware that offered routes to freedom.

Food for the Soul – Sites to Visit

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A Spectacular, Fascinating Natural Landscape

Today’s Chesapeake Bay, North America’s largest and most productive estuary, remains a dynamic natural system with humans as an integral part of its enormous six-state watershed.  Restoration of the Chesapeake Bay’s waters as habitat fish, crabs, oysters and other “living resources” – and the watermen’s culture that still follows their annual rhythms – is a natural challenge.

The Chesapeake Bay is young in geological terms, just 12,000 years old, the product of rising ocean waters following the last Ice Age that drowned the ancient valley of the Susquehanna River.  Scientists studying prehistoric evidence from pollens, bones and teeth of animals as mastodon and giant beaver have reconstructed the Delmarva Peninsula’s ultimate “lost landscape” deeply buried beneath wind-blown soils and sands as the Ice Age ended.  Other lost landscapes are more recent, as the rising waters inch by inch erode low-lying shorelines and wash away entire islands.

Visit Washington College’s Public Archaeology Lab or summer field school to learn about more lost landscapes being discovered by researchers.  Take the time to see Poplar Island, a lost island now recovered to 1,180 acres, rebuilt from silts dredged from Baltimore’s harbor.  The island is a popular site for birders and boaters delighted by the miraculous return of wildlife and waterfowl to what was once an empty horizon.

Take home memories and a new understanding of how everyone’s way of life affects their hometown watersheds.  Learn about the many efforts to improve water quality around the region.  Sign up for one of the many outdoor educational opportunities that put you “up close and personal” to the issues and critters in this unique marine environment.

Landscape – Sites to Visit

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African American Heritage

Maryland’s Network to Freedom includes safe houses of sympathetic African Americans and whites who risked their lives to help self-liberators reach freedom, and Civil War sites where some enslaved people fled to join the ranks of the Union Army.  It includes the shipyards, waterways, woods, fields and natural environments where freedom seekers hid, walked, fought and ran away.  In contrast, it also includes places that epitomized opposition to freedom, such as plantations where freedom seekers fled their enslavement and sites of captures, arrests, trials and jails where freedom seekers and their accomplices lost their struggles for freedom.  The Stories of the Chesapeake Heritage Area proudly shares the stories of local legends, Frederick Douglass and Harriet Tubman.

African American Heritage – Sites to Visit

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Trails and Byways

Bicycling Trails
| Driving Trails | Equestrian Trails | Walking Tours | Water Trails

Travel & Transportation… Past and Present

The rivers that thread the Stories of the Chesapeake Heritage Area’s landscape were both highway and barrier, depending on your point of view and the era.  American Indian villages existed on both sides of the waterways, yet later European settlers used rivers as the boundaries of their counties and towns.  Colonial rivers made it easy to get bulky tobacco to market in the Age of Sail, but crossings were a different matter. First, ferries and dams (and a few fords) marked crossings.  Then came bridges and railroad trestles, as railroads, and then highways, came to dominate the landscape.  Steamboat and rail lines following the Civil War opened the region to tourism as early as the 1870’s, when “summer visitors” came for the cooling breezes of the Eastern Shore.  Visitors later enjoyed resorts and amusement parks at Love Point on Kent Island and Tolchester and Betterton in Kent County.

Bicycling Trails


Driving Trails


Equestrian Trails


Walking Tours


Water Trails