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Captain John Smith was the first European to see and visit the Eastern Shore, in 1608. William Claiborne, who set
up a trading operation on Kent Island in 1631, developed the first settlement in Maryland. This was the third settlement in North America after Jamestown, Virginia, and Plymouth, Massachusetts. The colony on
which Claiborne landed was controlled by George Calvert, Lord Baltimore. He exercised all but sovereign power over his colony, Maryâs Land. Under his ãConditions of Plantation,ä he ordered the pattern
and means of settlement to assure its success and profitability.
Land patent-holders, friends, and trusted associates of Lord Baltimore brought settlers to clear and claim the
land. Early settlement was sporadic and precarious, but surprisingly rapid. Soon the need became great to create municipal centers throughout the colony to accommodate the legal needs of the growing
population. At first the colony consisted of one county, St. Maryâs. This was divided into ãHundreds,ä of which the Hundred of the Isle of Kent was the first. In 1642, the island and the northern section
of the Upper Eastern Shore region became Kent County. Talbot County was divided from this in 1662 and included all the area from the Chester River to the Choptank River. Queen Anneâs County was created
from Talbot in 1706, and Caroline County was divided from Talbot and the northeast part of Dorchester in 1773.
Many early settlers came to the Maryland colony to escape religious persecution. Quakers, Catholics, and others found
the Upper Eastern Shore to be a haven, allowing them to develop their faith in relative peace. There are no numbers to say how many people came to this area in the 17th and 18th centuries seeking religious
toleration. However, the multitude of churches found in this region attest to the religious ambitions of the people who settled here. Some of these churches are among the oldest surviving structures in
Maryland.
The rest of the colonists living in this area came to the Upper Eastern Shore for a new life and new
opportunities. Farming provided the principal opportunity for them to make a living. Across the region settlement centered around the farms and small plantations that grew swiftly on the profits of
planting tobacco. Introduced by Native Americans and sent to Europe, tobacco became very popular, and the demand grew quickly enough to sustain the general economies of Maryland and Virginia up to the end of
the 18th century.
The production of tobacco, a very labor-intensive plant to cultivate, required the steady influx of cheap labor into the
colonies. First this demand for labor was met with indentured servants, who paid for their passage to the colony with seven years of labor. Around the end of the 17th century, slave labor became a
dominant contributor to tobacco cultivation. More profit could be realized by enslaving a person for life than by using him for seven years. The slave population of the Eastern Shore grew steadily
throughout the colonial period.
Most settlement occurred along the waterways. The lives and economies of the colony required trans-Atlantic
shipping. Raw materials and agricultural products produced in the colony were traded for manufactured goods produced in Europe. Trade and transport required the safe harbors that rivers
provided. Because water-borne transportation was easier and safer than overland travel, roads were slow to develop across this region. Most large houses, such as Wye House in Talbot County
(National Historic Landmark), were built close to the water. Each large plantation had wharves where agricultural goods were loaded for shipment. Most such goods were shipped directly to Europe.
Tobacco, however, was gathered and inspected in warehouses in such towns as Chestertown or Denton before shipment
abroad. Fluctuations in overseas markets wildly affected fortunes of local planters. One method to stabilize profits was to inspect all stocks of tobacco. Only tobacco of a certain quality was
shipped abroad. Substandard tobacco was burned on site. This allowed the planters some control over the quantity and quality of tobacco shipped. None of these tobacco warehouses remain today.
Chestertown, Centreville, Easton, and Denton were established as county seats, centrally located within their
counties. They grew around their courthouses and provided a gathering place for county residents to meet, share gossip and news, conduct business, and seek justice. Taverns, hotels, and shops were constructed
to serve the farmers, watermen, and sailors who congregated to do business, trade goods, and create the Eastern Shore culture and lifestyle. Easton grew to become the largest town on the Upper Eastern
Shore. It boasts many of the areaâs first achievements, including the Eastern Shoreâs first newspaper (1790), bank (1805), and steamboat line (1817).
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