4. Charlottesville, Virginia
Population: 225,531
College: University of Virginia
Charlottesville snagged number one for its lively cultural scene. Some of the numerous attractions that the town is known for include its wine and beer tours, the homes of Thomas Jefferson, James Madison and James Monroe and nearby scenic Shenandoah National Park. The town’s claim to fame is that it is both the home and launching pad of the Dave Matthews Band.