Long Weekend
3 days · ~160 miles · from Charlottesville
Monticello and Montpelier with the Monticello AVA poured between them, then Virginia's prettiest road north — grafting onto the Civil War loop at Orange for a battlefield chaser.
This trip chains: The Constitution Route & 231 · Bull Run to the Bloody Angle
Monticello's first tour, Michie Tavern fried chicken, then two Monticello Trail tastings (King Family if it's polo Sunday). Downtown mall dinner.
Octagon among the ruins at Barboursville, Gordonsville's Exchange Hotel and chicken history, Madison's Montpelier — then north on 231 through Somerset's horse country. Overnight Madison or Graves Mountain.
Morning pastures under Old Rag, coffee in Sperryville — then choose: Skyline Drive south, or east to Cedar Mountain and Brandy Station to join the Civil War loop where it crosses your path.