ARRIVING in Charlottesville from the lush, rural Virginia countryside, you almost feel like you've stepped back into ancient Rome. The Rotunda, the centerpiece of Thomas Jefferson's design for the University of Virginia, was of course built to resemble the Pantheon and the neo-Classical facades of the college buildings seem to be right out of Caesar's time.  But the town itself is far more cutting-edge than its architecture. As American regional cuisine has gone upscale over the past decade, Charlottesville has been at the center of many changes, with local chefs updating traditional Southern fare by marrying grits, fried chicken and other standbys with French, Asian and other influences. The town's music scene, too, has served up megastars like the Dave Matthews Band and helped to launch the modern roots-rock wave. Even Virginia wine, once more Burger King than Bordeaux, has caught on. Local vineyards that never used to get invitations to competitions now hold their own with the finest of California or France. Even Jefferson would be proud  the third president succeeded at nearly everything, but he couldn't coax a decent wine out of Virginia's soil.  3 p.m. 1) MALL RATS  Running through the center of Charlottesville, the pedestrian mall is lined with oak trees and packed with students kicking the Hacky Sack and talking philosophy over coffee. Start at the east end and take a long leg-stretcher along the mall. You'll pass rows of restored brick buildings, street mimes and violinists, a central plaza for public art, and al fresco cafes that make the street seem more European than American  something the Europhile Jefferson would have appreciated. Reflecting the local cuisine fascination, the mall also has become a grand eating fest, with places proudly featuring Virginia ingredients. Stop in just off the main mall for a snack at Feast (416 West Main Street, Suite H; 434-244-7800; www.feastvirginia.com), an artisanal cheese shop, charcuterie and gourmet market that could easily be found in Paris.  Along with the university, Jefferson's estate, Monticello (www.monticello.org), obviously draws many visitors to Charlottesville, but its grandeur and almost palatial setting make it seem more like a museum than a home. After the obligatory visit, try a more intimate presidential residence  Ash Lawn-Highland, the home of James Monroe, who even today still sits in Jefferson's shadow. Unlike Monticello, Ash Lawn seems as if it had just been lived in  just a simple family farmhouse still filled with Monroe's own keepsakes (1000 James Monroe Parkway; 434-293-9539; www.ashlawnhighland.org).  9 p.m. 3) HORSING AROUND  Only 10 minutes from downtown Charlottesville, the Clifton Inn (1296 Clifton Inn Drive; 888-971-1800; www.cliftoninn.net) feels more like Kentucky. Rolling hills and fenced-off pastures resemble classic horse country. In recent years, as Charlottesville's restaurant scene has gone upscale, Virginia's inns have also embarked upon a culinary arms race, and the Clifton Inn has kept up with the latest cooking weaponry. Its restaurant, inside a white-pillared Gone With the Wind-style southern mansion, offers a design-your-own tasting menu featuring local ingredients. Dinner for two with wine is about $150 and reservations are essential.  8 a.m. 4) JEFFERSON'S GENIUS  Early morning is the best time to appreciate Jefferson's architectural genius. Walking through the university campus at this hour, you'll find it nearly deserted. You can sit on the main lawn alone and marvel at the perfect symmetry of the Rotunda, a United Nations World Heritage site. The Rotunda sits at the north end of the lawn, surrounded by other pavilions, and the morning light makes the neo-Classical whites shine like a polished Army shoe. Free one-hour tours of the Rotunda are available five times a day (434-924-3239; www.uvaguides.org.  For a fascinating detour little known by outsiders, visit the university's Kluge-Ruhe Aboriginal Art Collection. Twenty years ago, John W. Kluge, a billionaire media mogul, started building perhaps the largest collection of aboriginal art outside Australia, which he donated to the University of Virginia in 1997. The museum offers free guided tours every Saturday at 10:30 a.m., which are essential to understanding these stark and sometimes inscrutable works of art (400 Worrell Drive, Peter Jefferson Place; 434-244-0234; www.virginia.edu/kluge-ruhe).  1 p.m. 6) WINE COUNTRY  Though Thomas Jefferson started the local wine industry, only recently have growers produced decent vintages. Virginia has 11 wine trails to explore and 136 wineries, many focusing on cabernet francs, which seem to adapt best to the local climate. Old House Vineyards (18351 Corkys Lane, Culpeper, Va.; 540-423-1032; www.oldhousevineyards.com) is 50 minutes from Charlottesville and has achieved renown for its Vidal Blanc, without developing the kind of attitude that sometimes pervades California. Tastings cost $5. For more information on Virginia vineyards, see www.virginiawines.org.  3 p.m. 7) COUNTRY ROADS  Head out for the afternoon by driving northeast along Route 20 toward Barboursville, a town almost in another dimension. (The area was the fictional locale for The Waltons on TV.) The drive, through an area called the Southwest Mountains Rural Historic District, winds up and down some of the most rural farmland in the state, all sitting in the mountains' shadow and crowned, in fall, by changing colors that match New England's. Keep your eyes out for historical marker signs, as the area also boasts a rich trove of African-American history (www.nps.gov/history/nr/travel/journey/sou.htm).  7 p.m. 8) DINING AMID THE RUINS  Stay in Barboursville and head to Palladio Restaurant, on the grounds of the Barboursville Vineyard (540-832-7848; www.barboursvillewine.net). Jefferson himself designed the main building at the vineyard, which dates back to 1814. Part of the original estate burned down in the late 1880s, but from the adjacent building, a sprawling Georgian villa, you can gaze at the ruins of Jefferson's marvel  or out into the sunset over the Southwest Mountains. The restaurant, which features Northern Italian cooking, also strives to go local, as when it pairs quail with Southern-inspired corn cakes. Reservations are essential. Dinner for two with wine is about $200.  10 p.m. 9) MILLER TIME  Every college town needs a few decent watering holes for grungy bands, but in Charlottesville, you wind up later seeing those bands on MTV. Most famously, the Dave Matthews Band got its start here, back when Mr. Matthews bartended at Miller's (109 West Main Street; 434-971-8511). He might have since moved on to arenas, but Miller's, a converted drugstore that retains the trappings of an old-time apothecary, is still there, favored by local music fans for its eclectic array of bands. Get there by 10 before the college crowd packs the place, and try to catch the one night a week when the famed bebop jazz trumpeter, and local music professor, John D'earth headlines the bill.  9 a.m. 10) HIT THE TRAIL  Coming to Charlottesville, many visitors take a side hike in Shenandoah National Park. In summer, Shenandoah's Skyline Drive seems more like Los Angeles at rush hour. But by late fall, a time when the leaves are still changing in Shenandoah, the crowds thin out, and it's easier to find solitude. Head to the Appalachian Trail, which runs adjacent to Skyline Drive, and which draws even fewer weekend crowds. For information on the Appalachian Trail in Virginia, see www.appalachiantrail.org/virginia.  11 a.m. 11) FUEL UP  Back in town, restore the calories you burned hiking  and pack on way more  at the Bluegrass Grill and Bakery (313 Second Street, SE; 434-295-9700) for brunch. Not much nouveau cuisine here. Plan on hearty Southern comfort fare  cheesy grits, buckwheat pancakes, heavenly home fries and fluffy homemade wheat biscuits that taste like someone added an entire stick of butter to each one. Bluegrass takes no reservations, so be prepared to wait for a table. Brunch for two costs around $35.  US Airways offers nonstop service between La Guardia Airport and Charlottesville-Albemarle Airport. The round-trip fare is around $500, according to a recent Web search.  Besides its restaurant, the Clifton Inn (1296 Clifton Inn Drive; www.cliftoninn.net; 888-971-1800) has 18 lush guest rooms and suites on a 100-acre property with walking trails, tennis, a pool and hot tub. Rooms start at $205.  For a less expensive alternative, try the 200 South Street Inn (200 South Street West; (434-979-0200; www.southstreetinn.com). Right in the center of town, the inn is a stately mansion dating in part to 1852, with 19 guestrooms and personal touches, like wine and cheese plates in the afternoon. Rooms start at around $150.  Check the University of Virginia schedule for parents' weekends and major events ; during these times it may be nearly impossible to get a room anywhere near Charlottesville. A calendar of the University of Virginia academic year is at www.virginia.edu/registrar/calendar.html.
Though it’s known for its neo-Classical architecture, this Southern town’s innovative culinary and music scene would make Thomas Jefferson proud.