Townies and University of Virginia students harmoniously coexist in the two unique sides of Charlottesville: Downtown and the Corner. “The Corner is the university side with all the dive bars and cheap food,” a recent grad explained to us. “Downtown is where all the nicer restaurants are.”

And Downtown is where you’ll want to be on weekend evenings in the summer, when things really gets hopping. Directly off the red brick–paved pedestrian mall, the Charlottesville Pavilion (321 E Main St, 434-817-0220, charlottesvillepavilion.com) hosts the Fridays After Five (pictured) concert series—free music events every Friday night. At First Fridays (the first Friday of each month, through September) the mall’s independent galleries offer gratis drinks and nibbles for concertgoers—a range of personalities from golden retriever–walking middle-aged dads, to sweatshirt-clad students, to local celebs like Sissy Spacek, Dave Matthews and The Rock (who live a happily mellow and paparazzi-free life among the locals).

For eats, there are plenty of excellent high- and low-end options. Hit the budget-friendly Bluegrass Grill & Bakery (313 2nd St SE, 434-295-9700) for one of the city’s most-popular brunches and order one of the biscuits, made with a blend of regular and whole-wheat flours, with your meal. The wait will likely be at least an hour, so walk a few short blocks to the Saturday-morning Charlottesville City Market (pictured, April to October from 7am to noon, Water Street parking lot), where you can sate your rumbling stomach with the fresh samples from dozens of nearby farms, plus try fried-in-front-of-you doughnuts and freshly brewed Shenandoah Joe fair-trade coffee. We even tried raw sheep’s milk cheese—which has been banned by the USDA—from a farmer who couldn’t bear to stop making it even though he technically can’t sell it (he will, however, accept donations). Find fancier grub at Mas (501 Monticello Rd, 434-979-0990), known for its creative tapas menu, or OXO (215 W Water St, 434-977-8111), a dimly lit, contemporary American spot where the hip and the beautiful sip neon-hued cocktails at the bar until late into the night.

Übercheap lodging options abound, like BYO-hair dryer (and soap…) Red Carpet Inn (405 Premier Circle, 434-973-8133, rooms start at $68), but for a swankier, B&B-style experience, spend at least one night at the charming, 18-room The Clifton Inn (1296 Clifton Inn Dr, 434-971-1800, rooms start at $325 in high season) a few miles outside of town. After a cocktail at the bar and some fresh soft-shelled crabs (there’s a nightly tasting menu), you’ll fall into your cozy feather bed full but not stuffed.

Wherever you stay, you’ll want to spend an afternoon hiking. Pick a path at charlottesville.org/trails and then drive out to the trailhead for a woodsy trek that might cross streams and pass waterfalls. Another option: brave the snaking county roads along the Monticello Wine Trail as you sample tastings at a few of the area’s 22 vineyards (for a full list, go to monticellowinetrail.org). Jefferson Vineyards (1353 Thomas Jefferson Pkwy, 434-977-3042) is ideally positioned around the bend from major tourist attraction Monticello (pictured, 931 Thomas Jefferson Pkwy, 434-984-9822), Thomas Jefferson’s home and plantation, where he grew grapes and brewed his own beer. The venue is a bit bare bones compared to the beautifully rustic digs and vast lawns of nearby Veritas (145 Saddleback Farm, 540-456-8000)—a shoe-in for a Martha Stewart Weddings spread. But the Jefferson staff was the friendliest we encountered, and we left with a few bottles of their Viognier, a full-bodied white. On your way up the driveway, grab a bulging sandwich to-go at Brix (1330 Thomas Jefferson Pkwy), a converted gas station that whips up homemade ’wiches that’ll leave you licking your fingers. As a Jefferson staffer told us, “The turkey is so fresh there, it should be alive.”

A visit isn’t complete until you’ve checked out the beautiful UVa campus, and the free trolleys running back and forth across town make it a cinch. You won’t get far before you experience the ubiquitous presence of “Mr. Jefferson,” as locals call our nation’s third president. Jefferson, who was famously proficient in the fields of landscaping and architecture (among many others), founded the school almost 200 years ago. His visually striking campus design—with its huge, lush lawns and stately, neoclassic brick buildings—will make you want to enroll in grad school on the spot.

And be sure to explore the museum housed in the school’s main library, where you’ll find one of the few surviving original signed copies of the Declaration of Independence. After drinking, hiking and eating your way through C-ville, it’s a fitting way to end a visit to a town steeped in history—you can’t help but get goose bumps.

THE TAB

Two nights, two people
Airfare $200*
+ Rental car $125
+ Hotel $405
+ Meals $200
TOTAL $930

*Southwest flies direct to Washington, D.C., for $100 round-trip, and it’s a scenic two-hour drive down to the city.