Founded in 1786, the former colonial resort of Charles Town (pop. 5,259) was named in honor of George Washington’s younger brother Charles, who surveyed the site on behalf of Lord Fairfax. Many of the streets are named after other family members, over 75 of whom are buried in the cemetery alongside the Zion Episcopal Church, on Congress Street on the east side of town. Charles Town, which shouldn’t be confused with the West Virginia state capital, Charleston, later played a significant role in John Brown’s failed raid on Harpers Ferry. After Brown was captured, he was tried and convicted of treason in the Jefferson County Courthouse at the corner of George and Washington Streets and hanged a month later. With his last words, Brown noted the inevitable approach of the Civil War, saying he was “quite certain that the crimes of this guilty land will never be purged away but with blood.” A small museum (Tues.-Sat. 11am-4pm, $3 adults) operates on the first floor of the town library, a block from the old courthouse on Washington and South Samuel Streets.

South of Charles Town, US-340 winds along the western slopes of the Appalachians for a dozen miles before entering Virginia east of Winchester.