Virginia's many lovely small towns capture and nurture the state's history and culture. This is especially true in the Shenandoah Valley, where I-81 and U.S. 11 follow the route of the colonial-era Valley Pike, thus continuing to string together Winchester, Strasburg, Staunton, and Lexington, all possessed of 18th- and 19th-century brick and stone buildings.
Middleburg: The self-proclaimed capital of Virginia's Hunt Country, Middleburg takes up barely 6 blocks along U.S. 50, small enough to be digested in an afternoon. Some of the world's wealthiest individuals keep their horses near Middleburg, and the town has a host of upscale shops in buildings dating from the 1700s.
Monterey: Over Shenandoah and Bull Pasture Mountains from Staunton, the village of Monterey appears more like New England than Virginia, with its white churches and clapboard homes in a picturesque valley. Thousands of visitors make the trek over the mountains to the annual Highland Maple Festival in March.
Staunton: There's Shakespeare to be seen at the Blackfriars Playhouse in Staunton, an old railroad town that was formerly most famous as President Woodrow Wilson's birthplace. The replica of The Bard's 17th-century indoor theater has spurred a downtown renaissance, with new restaurants and shops opening all the time. A don't-miss for kids, the Frontier Culture Museum is here, too.
Lexington: One of America's best small towns, Lexington has a lively college atmosphere in addition to a host of sights. It's home to the Virginia Military Institute (VMI), where Gen. Thomas J. "Stonewall" Jackson taught; its students went off to the Civil War at New Market. Afterwards, Robert E. Lee came here as president of Washington College, now Washington and Lee University. VMI was the alma mater of Gen. George C. Marshall, who won the Nobel Peace Prize for his plan to rebuild Europe after World War II. Jackson, Lee, and Marshall are buried here, and there are museums dedicated to them.
Abingdon: Daniel Boone opened Virginia's Southwest Highlands to settlement in the 1770s, and a thriving town grew up at Abingdon. Homes and buildings dating to 1779 line Main Street, making it a wonderful place to stroll. The town is home to the Barter Theatre, Virginia's state stage, where you can still barter for a ticket.
