Front Royal began as Lehew Town, a frontier village on the packhorse road to the east. According to local lore, its current name derives from the command by frustrated military officers for unruly troops to "front of royal oak," which once stood in the public square.

Belle Boyd, the Confederate spy who charmed military secrets out of her Union suitors, used Front Royal as one of her most effective bases. On May 15, 1862, Boyd overheard plans that the Union troops were exiting Front Royal and leaving behind only a small force. Boyd relayed this information to General "Stonewall" Jackson, and on May 23, Jackson lead his troops into town and the Battle of Front Royal ended with the capture of 750 of the 1,000 Union soldiers.