U.S. Route 41A passes through the center of town, coming in from the southeast as South College Street and leaving to the northeast as Dinah Shore Boulevard. US 41A leads east to Cowan and to Sewanee, as well as north to Estill Springs and to Tullahoma. Tennessee State Route 16 leaves southwest from the center of town as 1st Avenue and leads to the Alabama border. U.S. Route 64 bypasses Winchester to the south and east, leading northeast to Interstate 24 near Pelham and west to Fayetteville. Tennessee State Route 50 leads west and northwest from Winchester to Lynchburg, and Tennessee State Route 130 leads northwest to Winchester Springs and to Tullahoma.