[5] Seven commissioners were originally 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.

[6] Until the completion of these buildings, court was held at Melvill's Warehouse, approximately 1.5 miles (2.4 km) north of Pig Point.

[7] 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.

Retirees and workers willing to commute across the Chesapeake Bay to the western shore are increasingly attracted by the rural environment and low cost of living.

From 1994 to 2014 Caroline was the only county in the state not represented by a resident legislator in the Maryland General Assembly.

Indeed, the last Democrat to reach forty percent of the county’s vote was Jimmy Carter in 1980.

In earlier times Caroline was a swing county,[13] less secessionist than Wicomico, Worcester, Queen Anne’s or Cecil.

Notable waterways include the Choptank River and Tuckahoe Creek, as well as the man-made Williston Lake.

Caroline County currently ranks seventh nationally in terms of land protected under the Ag Preservation Program.

Caroline is the only Eastern Shore county not to touch either the Chesapeake Bay or Atlantic Ocean.

Additionally, it is the only county on the Eastern Shore without an Interstate or United States Highway within its borders.

As of the 2010 United States Census, there were 33,066 people, 12,158 households, and 8,702 families living in the county.

It is chiefly used in the summertime by non-local beachgoers heading to Ocean City, Maryland, or Rehoboth Beach, Delaware.

The United States Census Bureau recognizes three Census-designated places in Caroline County: