The settlement that would become Romney began as Pearsall's Flats, a riverside plantation worked by Job Pearsall and his brother John from the 1730s. After Braddock's defeat in 1755 the brothers fortified their property as a stockade - Fort Pearsall - and the Virginia Regiment, under the young Colonel George Washington, used it as part of a string of frontier forts during the French and Indian War. With the war over, Thomas Fairfax, 6th Lord Fairfax of Cameron, recognized the value of the South Branch valley and in 1762 sent surveyors to lay out the town in 100 lots. He named the new town Romney, after the Cinque Ports city on the English Channel. The Virginia Assembly chartered Romney along with Shepherdstown on December 23, 1762 - making them the oldest incorporated towns in what would become West Virginia.

Romney's strategic position - on the Northwestern Turnpike connecting eastern Virginia to the Ohio Valley, on the South Branch Potomac River, surrounded by lowland farms in a county that voted against secession - made it valuable to both sides during the Civil War. By some local counts the town changed hands more than fifty times between Union and Confederate forces. Some changes were major occupations; others were dragoon raids that flipped the flag for a day. The constant turnover left scars. The Romney Literary Society's library of 3,000 volumes was scattered or destroyed by Union troops, and only 200 books were salvaged after the war. The Fort Mill Ridge Civil War Trenches just south of town - dug by Confederate artillery in 1861-62, refurbished by Union infantry in 1863, and held by the Union for most of the war - survived because the ground was too steep to farm.

Despite the war, Romney built itself into something unusual for a mountain county seat. In 1819 the Romney Literary Society was founded - the first organization of its kind in present-day West Virginia, and one of the earliest in the country. In 1820 it pushed Romney Academy to add classical languages, making it the first institution of higher education in the Eastern Panhandle. The 1846 Classical Institute building became, after the war, the campus of the West Virginia Schools for the Deaf and Blind, which still operates today. In 1867 the town raised what it claims is the first Confederate memorial in the country - the marble obelisk that still stands at Indian Mound Cemetery. In 1870 the Literary Society built Literary Hall on West Main Street, rebuilding the library it had lost in the war. Layer by layer, Romney became the kind of small Allegheny town that produced an outsized share of West Virginia public intellectuals.

Romney still has no public transportation. No train. No bus. No commercial airline service. The town sits on U.S. Route 50, a two-lane east-west highway that meanders across the Appalachians. It is about one hour from Winchester, Virginia, on I-81 to the east, about one hour from Cumberland, Maryland, on I-68 to the north, and roughly 2.5 hours from Dulles International Airport. The seven-mile South Branch Potomac gorge known as The Trough lies just south, and the Potomac Eagle Scenic Railroad runs excursion trains through it from a station near downtown. The Hampshire County Convention and Visitors Bureau operates from the Bottling Works building at 426 East Main Street. The town that Lord Fairfax surveyed in 1762 is still small enough to walk in an afternoon, but contains more layers of American history per block than nearly any other settlement of its size in the country.