Long weekend getaway recommendation: Charlottesville VA.
Fly to Richmond (2hrs). Rent a car and drive to Charlottesville (1hr). Stay in the Keswick Hotel. Go to Monticello, and Monticello Vineywards. Walk around the University Grounds. Visit King Family Vineyards. Have brunch at Fossett’s (best bacon of my whole life, really). Visit Barboursville Vineyards. Go for a hike or drive in the mountains.
Amazing, easy weekend trip from NYC.