DISTANCE: 161 miles; 3 hours, 16 min.
YOU WON'T WANT TO MISS: Start at the center of town, which boasts a long outdoor plaza-mall at 610 E. Main St., full of cafes, markets, restaurants and shopping. For an old-fashioned theater experience, try The Paramount (theparamount.net), which has a schedule alternating between movies and concerts. History buffs must make the pilgrimage to Thomas Jefferson's home, Monticello (monticello.org). And we have to mention that there are many wineries close by, even one, Blenheim Vineyards, (blenheimvineyards.com) owned by Dave Matthews. Yes, that Dave Matthews.
IF YOU DO ONE THING: See a live show. Charlottesville's renowned for its music scene. The Charlottesville Pavilion (charlottesvillepavillion.com) has a packed summer schedule, as does the more indie Jefferson Theater (jeffersontheater.com).