When traveling from Winchester to Charlottesville in Virginia, take Route 522 South through Sperryville. From Sperryville, take Route 231 to Madison where you will pick up Route 29 for the rest of the trip. The stretch of road from Sperryville to Madison is one of the prettiest drives you will see in this part of the country, especially in the Spring and Fall. It goes just east of the Blue Ridge Mountains. Nice, gentle Virginia countryside. While in Charlottesville, visit Thomas Jefferson's masterpiece - the University of Virginia - the prettiest college ever. That visit needs to be done right about now. May is the best month in C'ville.