Since the basis for Maryland’s economy was crop export, and especially tobacco, becoming successful required hiring or obtaining laborers to work the land. Tobacco farming was very labor intensive. At first colonists imported poor people from England who worked for a term of years in exchange for their passage. Starting in the late seventeenth century, colonists began to import enslaved people from Africa and the Caribbean in increasing numbers as an alternative to indentured labor, convict servants, and day laborers.

Not everyone who was successful grew tobacco. In 1709, for instance, David Macklefish, a prominent citizen, referred to himself as the “Lord Mayor of London” because he owned more lots in town than anyone else. In the same year, Edward Rumney received an ordinary license, which allowed him to keep a tavern and to sell alcohol. The town must have been quite busy to support his new business, as well as the three or four others already in operation, including one owned by the Holland Pierpoint family.