The Town of Hillsboro was founded in 1784 and is one of Caroline County’s oldest towns. Although the Town was settled in the late 1700s, the first bridge crossing the Tuckahoe River to the hamlet that was to become Hillsboro is referenced as early as 1706. Hillsboro is located near the Tuckahoe River on the border where Caroline County meets Talbot and Queen Anne’s Counties. Most of its historic character has remained intact and is cohesive, a circumstance that is proving to be a valuable economic commodity for modern towns on the Eastern Shore.