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The winner of our 4/28/2025 Town election was Sandy Higdon with 13 votes
Hillsboro, Maryland
Quaint, Cute, Comfortable
Founded in 1784, Hillsboro, Maryland is not only recognized as Caroline County's oldest incorporated town, but is also the home to many firsts, including the County's first school and newspaper.
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.
