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During the colonial and early national period, the Upper Eastern Shore was a major economic center in the New
World. The third-oldest European settlement in North America was established on Kent Island in the 1630s. Men and women sailed over to create new lives in the new world. Many came seeking their
fortune in the production of tobacco. Others sought relief from religious persecution. Many came as indentured servants leaving harsh lives behind in the mother country. Still more were brought as slaves
from their homeland to harsh lives in the fields. For 160 years, Europeans (mainly English) and Africans lived in this region, settled along its waterways, built its county seats, and established the culture
that today still defines Marylanders of the Upper Eastern Shore and their way of life.
A striking number of structures survive from the colonial period and the early years of the nation. Chestertown, second
only to Annapolis in the number of 18th-century structures in its historic district, contains more than 50 built before 1800
Across the region, sturdy brick homes, mills, courthouses, and old roads remain from this period.
Railroad Towns of the Upper Eastern Shore
Caroline County
- Denton
- Bethlehem
- Federalsburg
- Greensboro
- Goldsboro
- Henderson
- Hillsboro
- Marydel
- Ridgely
- Preston
Kent County
- Chestertown
- Hepbron
- Kennedyville
- Massey
- Millington
- Worton
Queen Anneās County
- Centreville
- Barclay
- Carville
- Grasonville
- Price
- Roberts
- Stevensville
- Sudlersville
- Willoughby
Talbot County
- Easton
- Cordova
- McDaniel
- Oxford
- Queen Anne
- St. Michaels
- Trappe Station
The greatest concentrations of colonial-era sites lie along the major rivers. Colonists came by boat and settled
near the water. Most prominent among these are the Chester, the Miles, and the Choptank Rivers. Each county seat contains colonial-era sites. Because of the need for access to water for colonial
settlements, such sites, like the water-oriented sites, are found in the western section of the Upper Eastern Shore with a few inland sites in the east.
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