Hillsboro Business Directory

Hillsboro is a small community at the border of Caroline, Queen Anne's, and Talbot counties, with a population of roughly 200 residents. Originally established as a crossroads community in the early 19th century, Hillsboro retains a quiet rural character anchored by small farms and local service businesses. The community is home to the Caroline County Fairgrounds, which hosts the annual Caroline County 4-H Fair, one of the largest agricultural fairs on the Eastern Shore. The surrounding countryside produces grain and produce, and the fairgrounds are a significant community gathering space throughout the summer season.