As any University of Virginia grad will breathlessly assert, Charlottesville, VA is America's greatest college town. Perhaps even the world's. (Oxford? Bah!) Even this state-school graduate must admit there's a case to be made. C'ville, as it's known, is a lovely and vibrant little town rich with history, thanks in no small part to UVA's spacious, rolling grounds that have been painstakingly preserved since the university's founding in 1819. But there's more to Charlottesville than just UVA (and its famous Corner, a stretch of shops and eateries where students gather to slop down cheap, serviceable sustenance).

A mile down the road, the Historic Downtown Mall is one of the nicest pedestrian promenades I've ever seen. Unlike many other "downtown revitalization" projects, this is the real thing—those are real 19th-century buildings, not facades built in the 90s. It's also popular with locals who come to shop at Oysterhouse Antiques (featuring imported and restored East Asian antiques at wholesale prices), drink at Miller's Downtown (an old-man bar with an 80s punk soundtrack) and catch touring acts at the Jefferson Theater.

The real attractions sit just outside of town. Of course, no trip to Charlottesville is complete without a tour of Monticello, the mountaintop mansion built by Thomas Jefferson, Charlottesville's favorite son and founder of the university. This World Heritage Site is more than just a restored old house. (And it's far from tourist trap.) Rather, it's a living museum dedicated to one of America's greatest thinkers. Opt for the Behind the Scenes tour, which takes visitors to the once-verboten upper floors, and leave time to meander through the sprawling gardens.

Then, it's an afternoon dedicated to the area's plonk. Dozens of vineyards are tucked away in these rolling hills, and they range from small family-run weekend operations to big names on the international scene. A short drive from Monticello, Blenheim Vineyards has been turning out mid-range reds and whites since 2000 when it was established by C'Ville's other favorite son, Dave Matthews. Yes, that Dave Matthews. Blenheim's timber-frame tasting room and southern-exposure terrace can't be beat. Tastings are just $5 and include sips from several bottles. Thirsty for more? Ask a staffer for recommendations. You can't drive a mile without stumbling upon another vineyard, so local expertise is invaluable.

Once you've had your fill, set your GPS for the Clifton Inn, where chef Tucker Yoder is making waves with his almost-but-not-quite molecular gastronomy. His small-plates menu is divided according to each dish's body (delicate, light, full bodied, robust) and diners are encouraged to plan their own courses. We enjoyed following the incredible (and, yes, quite robust) sweetbreads with a lighter leek and potato soup. The best wine pairings, naturally, feature local bottles.

Jeff Koyen is a freelance travel and culture writer. Follow him on Twitter: @jeffkoyen.