Winnsboro Share definition Flag The shittiest town in Fairfield county. Known for crooked cops, ignorant people, Wal-Mart, and it's shitty school district. Hey, Winnsboro sucks. Winnsboro by A.L.W. May 29, 2008 0 0 Get merch Get the Winnsboro mug. Buy Now — $32.95 See more merch