It's 1967 when Natalie Winslow discovers the diary of her great-great-grandmother and her eyes are opened to the history which shaped the prevailing attitude towards segregation in her hometown and surrounding areas. The town of Greensboro is located in Caroline County, Maryland, the only Eastern Shore county not to touch either the Chesapeake Bay or Atlantic Ocean. It is the second-smallest county by total area in Maryland. Notable waterways include the Choptank River and Tuckahoe Creek.
Its eastern border is the Mason-Dixon line, which is usually associated as the delineating line between the North and the South. A crownstone of the Mason-Dixon Line is located in Marydel. The dividing line was surveyed in the 1760's by Charles Mason and Jeremiah Dixon to settle the contradictory land claims of the Penn and Calvert families. Caroline County's eastern border was marked by 36 stones placed at one-mile intervals, while every 5 miles Crownstones were placed.
Caroline County was created in 1774 from parts of Dorchester and Queen Anne's counties. The county derives its name from Lady Caroline Eden, wife of Maryland's last colonial governor, Robert Eden. At the time of its creation, seven commissioners were appointed: Charles Dickinson, Benson Stainton, Thomas White, William Haskins, Richard Mason, Joshua Clark, and Nathaniel Potter. These men bought 4 acres (1.6 ha) of land at Pig Point (now Denton) on which to build a courthouse and jail.[
Until the completion of these buildings, court was held at Melvill's Warehouse, approximately 1.5 miles (2.4 km) above Pig Point. Elections and other business transactions were completed there, and the town became the center of the county. The first court session was held on March 15, 1774, at Melvill's Warehouse. In 1777, court was moved to Bridgetown (now Greensboro), but in the interest of convenience, court was moved back to Melvill's.
Disagreements arose concerning the permanent location of the county seat. The General Assembly reached a compromise in 1785 and ordered that 2 acres (0.81 ha) of land at Melvill's Landing should be purchased for a courthouse and jail. In 1790, the county court and its belongings moved to Pig Point. The Caroline County Courthouse was completed in 1797.
The county has a number of properties on the National Register of Historic Places. The National Park Service is developing a site in the southern half of Caroline County dedicated to interpreting the Underground Railroad as part of the Harriet Tubman Underground Railroad National Monument.