The annual Tomato War is a charity event that defines the spirit of Jessamine County. The competition pits Nicholasville residents against Wilmore residents hurling tomatoes until one last unstained soldier remains. A tug of war through the mushy aftermath usually follows. Proceeds go to Jessamine County's Helping Hands Organization.

The Tomato War's popularity is increasing, with more participants, and more media coverage, including the Pittsburgh Post-Gazette, Good Morning America, Ripley's Believe It Or Not, and Doonesbury.

The event is perhaps inspired by eastern Spain's annual La Tomatina.