Middleburg, VA
Middleburg, Virginia, the Nation's Horse and Hunt Capital, is a town of fewer than a thousand people in Loudoun County hunt country, founded in 1787 on the road between Alexandria and Winchester. Washington Street holds an inn that has taken guests since 1728, a national sporting library, oyster bars and galleries, with wineries and a Five-Star resort at the edges. Dulles is 21 miles away. Bring boots, and book December early.