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Come spend the weekend with Caroline!

Hillsboro

Chronicled in Frederick Douglass’ famous 1845 autobiography, this community evolved as a tobacco-trading center on Tuckahoe Creek. Hillsboro was the setting for several important events in Douglass’ life including the permanent separation of his family among slaveholders. Hillsboro is also the home to the county’s first fire company founded soon after a devastating fire destroyed East Main Street in 1896. Mostly residential, Hillsboro celebrates old-fashioned annual events including the community picnic, town-wide lawn sale and fireman’s parade.

Hillsboro