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The Maryland Heritage Areas Authority measures the viability of a potential heritage area by the presence of resources
of statewide significance. These include historic districts listed or eligible for listing in the Maryland Register of Historic Properties and natural or recreational resources of statewide significance.
The Upper Eastern Shore enjoys a great number of such resources.
Historic Districts
On the Upper Eastern Shore, there are six historic districts listed in the Maryland Register of Historic Properties.
Each district contains a collection of historically important structures and sites. Combined, these districts contain hundreds of significant resources.
Betterton Historic District, Kent County: Betterton is a small town in northern Kent County, on the banks of the
Sassafras River. The historic district occupies the core of the town. Betterton became a resort town early in its history. Many of the structures of the historic district were built when the
steamboat brought visitors to this popular resort. Today, Betterton is known for its public beach, one of the few places around the Chesapeake Bay providing swimming access.
Chestertown Historic District, National Historic Landmark, Kent County: Chestertown is the contemporary
county seat of Kent County. The county seat moved to Chestertown from Quaker Neck in 1707. The presence of the courthouse sparked the growth of the port town. The historic district includes much of
the central business district and surrounding residential areas of the 18th and early 19th centuries including the Customs House, Widehall, Emmanuel Church, and several structures of Washington College. Because of
the importance of the town in the colonial period, and because the historic district retains a high degree of historical integrity from the 18th century, the Chestertown Historic District has been designated a
National Historic Landmark.
Denton Historic District, Caroline County: Denton was established as the county seat on the high ground
above the Choptank River when Caroline County was established in 1773. The historic district encompasses most of the downtown area, including the historic Caroline County Courthouse and square. The
square is lined with many residential and commercial structures. Denton has been a major, regional hub for the distribution of agricultural products since it was founded in the late 18th century.
Easton Historic District, Talbot County: Easton was established as the county seat near the Tred Avon
River. A regional commercial and cultural hub, Easton has grown to become the largest town on the Upper Eastern Shore. The historic district encompasses the commercial and residential structures of the
downtown area, including the colonial-era Talbot County Courthouse and the 20th-century Avalon Theater.
Stevensville Historic District, Queen Anneās County: Stevensville was the major commercial center for Kent
Island for most of its history. Despite a great influx of development on the island and in nearby Kent Narrows, the historic core of the town is largely intact. The historic district includes this core
and such features as the Lowery Hotel, Cray House, and Christ Church. While it is little more than a crossroads town today, Stevensville, on the rail line from Love Point east to the mainland, was a center of
community life on Kent Island in the 19th century.
St. Michaels Historic District, Talbot County: St. Michaels enjoys a long maritime history due to its
natural harbor. It became an important shipbuilding center early in its history. The main street through town has remained largely intact thanks to strong preservation and marketing efforts over the last
few decades. The historic district includes the commercial area along the main road and the surrounding neighborhoods. Today, the historic district is one of the most popular tourist destinations on the
Eastern Shore.
In addition to these historic districts, the Upper Eastern Shore possesses 127 structures, boats, and sites listed in
the National and Maryland Registers. Six have been designated as National Historic Landmarks (NHL):
- Edna E. Lockwood,
Chesapeake Bay Bugeye, Talbot County. This craft exhibits 9-log construction, the oldest form of construction for indigenous Chesapeake Bay watercraft. Constructed in 1889 in Talbot County, she is the only surviving bugeye to retain the integrity of sailing rig and working appearance.
- Chestertown Historic District, Kent County. Founded with the establishment of the courthouse in 1707,
Chestertown was the largest town on the Eastern Shore throughout the 18th century.
- Hilda M. Willing, Skipjack, Talbot County. Built in 1905 with a V-bottomed hull, she is one of the
oldest skipjacks still dredging oyster beds, and one of the few remaining members of the last commercial sailing fleet in the United States.
- Kathryn, Skipjack, Talbot County. Built in 1901, she differs from the Hilda M. Willing in that her hull is
round, a rare construction. Like the Hilda, she continues to work the oyster beds of the Chesapeake Bay.
- Nellie Crocket, Oyster Buy-boat, Kent County. Constructed of wood in 1926, she transported produce and was
used to process oysters. For three years during World War II, she served the U.S. Coast Guard as a fireboat serving Washington, DC, Baltimore, and Norfolk, Virginia.
- Wye House, Talbot County. Built in 1781 to 1784, this house is an example of a large southern frame
plantation house with seven-part Roman Country House construction. Much of its significance derives from the prominent Lloyd family who built and continue to occupy it.
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