Locals proudly call Charlottesville Mr. Jefferson's town, and his legacy is everywhere. Walk the colonnades of the Academical Village he designed at the University of Virginia, a UNESCO World Heritage Site, and tour Monticello, his hilltop home, with its gardens and sweeping views. Nearby, you can also visit Highland, the home of President James Monroe, whose property Jefferson helped him choose.

But C-Ville is far more than a history lesson. Its young, diverse population brings a lively energy, with great coffee shops, a walkable Downtown Mall full of restaurants and shops, and a summer concert series at the outdoor pavilion featuring rising musical talent. The surrounding countryside is dotted with wineries in the foothills of the Blue Ridge Mountains, and the scenery is especially beautiful in fall.

Charlottesville is easy to reach from Washington, D.C., and Richmond and pairs beautifully with Shenandoah National Park. I'll plan a getaway that balances history, wine country and the mountains.