Originally called LeHewtown (after Peter LeHew, a French Huguenot who purchased 200 acres here in 1754), the Town was later purchased by a group of real estate speculators who arranged to have it incorporated as Front Royal in 1788. Rail service was established in 1854 with the construction of the Alexandria, Orange and Manassas Gap Railroad between Manassas and Riverton. This line was soon extended to Strasburg in time to become a factor in the Battle of Front Royal on May 23, 1862 and throughout the Civil War. Lumber, agriculture, manufacturing and grain mills provided employment in the region for decades after the Civil War.

The origin of the name "Front Royal" remains uncertain. There are currently two versions as to its source of origin. One being that, in early decades of European settlement, the area was referred to in French as "le front royal," meaning the British frontier. French settlers, trappers, and explorers in the Ohio Territority of the mid-1700's were referring to the land grant made by King Charles II, then in control of Thomas, Lord Fairfax, Baron of Cameron. In English, "le front royal" is translated to the "Royal Frontier."

However, the more colorful and legendary origin has it that during colonial days, a giant oak tree - the "Royal" Tree of England - stood in the public square where Chester and Main Streets now join. It was there that the local militia, composed of raw recruits slow to learn military commands and maneuvers, were drilled. On one occasion, the sorely tired drill sergeant became so exasperated by the clumsy efforts of his troops and their failure to follow his command that he hit upon a phrase that all could understand and shouted, "front the Royal Oak!" Among the spectators was a Mr. Forsythe who had been a professional soldier. He was so amused by the officer's coined order that he and his friends found much sport in telling the story, repeating "front the Royal Oak" until Front Royal was the resulting derivation.