Chipley, FL

Chipley, the Washington County seat, sits in Florida's Panhandle along State Road 77, about 100 miles northwest of Tallahassee. Most visitors arrive via US Highway 90 or I-10 (exits 120 or 130), with direct routes from Panama City Beach, Dothan, and DeFuniak Springs. The city hosts the annual Panhandle Watermelon Festival, featuring what locals call the world's largest watermelon auction.