Leitchfield was laid off in 1810 and named for David Leitch, a prominent landowner and founder of Leitch's Station. His estate gave land for Grayson's county seat. The site was chosen because of fresh water springs, particularly Big Spring nearby. Grayson's first circuit court met under a large oak tree on this hill, with Judge Henry P. Broadenax presiding. The town was incorporated in 1866.