In the heart of southern Ohio, the city of Portsmouth knows how to make the holiday season memorable. Each winter, this riverfront community transforms into a scene straight out of a Hallmark movie—complete with twinkling lights, horse-drawn carriages, and cozy family traditions. But Portsmouth’s Winterfest doesn’t just celebrate the season. It makes history doing it.

As the air turns crisp and snow blankets the landscape, Scioto County transforms into a winter wonderland filled with enchanting...