Hillsboro is the county seat and Highland County’s largest community, featuring Ohio’s oldest county courthouse still in operation. The beautiful Greek Revival courthouse dates back to 1834 and is Ohio’s oldest courthouse in continuous operation. The city was plotted with wide streets and the main thoroughfares are adorned with large and beautiful homes.

All of Hillsboro’s streets seemingly lead “uptown” to the business district, and with historic restorations and new construction in recent years the community is undergoing something of a renaissance. A host of thriving businesses serve the needs of residents and visitors alike.

Several Hillsboro residents have risen to prominence, including former Governor Allen Trimble, cartoonist Milton Caniff, women’s temperance leader Eliza Thompson and sportswriter Hugh Fullerton.

Prominent activities in Hillsboro during the year include the Festival of the Bells in early July, the Christmas parade in December, and more intimate activities such as the Chocolate/Wine Walk sponsored by the Hillsboro Uptown Business Association.

The Highland County Historical Society is headquartered in Hillsboro and is very active in curating the area’s rich history. One such project is called “Voices from Lincoln,” about the old Lincoln School attended by African-American students during times of segregation. The society was also involved in updating and expanding Elsie Ayres’ history originally written for the city’s 1957 sesquicentennial. “The Hillsboro Story” is now in its third printing.