Introduction

You don’t need a PhD in Architecture to appreciate Charlottesville. But a nose for aesthetics sure helps. It’s the nuances that make C’ville so intriguing. Like the antique soda fountain that stirs vanilla malts at Timberlake’s Drug Store. Or the rumbling boxcars that shake bottles in the basement bistro at C&O Restaurant. Or the faded-white Pepsi mural across the tracks. I always bring my camera when I travel to Charlottesville.

Sublime elegance defines the area’s two main attractions: Thomas Jefferson’s dual compounds of Monticello (his home) and the University of Virginia (his love). His architectural genius reveals itself in the details—Greco-Roman friezes above Monticello’s doorways; uniquely manicured gardens behind the pavilions on UVA’s campus.

Charlottesville’s genteel past is complemented by a progressive now. Like a second-generation hippie, C’ville has shed its formerly crunchy ethic and embraced hipster fineries—Spanish tapas, tequila bars, granite countertops, and tattoo art. But the secret is out: the smart set now knows Charlottesville has evolved into one of America’s most underappreciated and livable cities—you won’t be the only one scanning the local real estate ads.

See and Do

The Layout: Think of Charlottesville as a dumbbell, with the University of Virginia (UVA) the western weight, the revitalized Downtown Mall the eastern, and West Main Street acting as the handle linking the two. UVA and Monticello, Thomas Jefferson’s masterworks, are listed as UNESCO World Heritage Sites.

Jefferson was as proud of founding the University of Virginia as he was of penning the Declaration of Independence. No surprise that both have weathered the centuries with elegance and distinction, and yield new wisdoms with each studying. An architectural museum as envisioned by Jefferson, UVA’s centerpiece is the beguiling, expansive Lawn, the communal green space around which the campus was built. Bookended to the north by the Romanesque Rotunda and to the south by Cabell Hall, the Lawn plays host to all seasons of a student’s life, from orientation to commencement. Along the Lawn, venerable pavilions house faculty and a few choice seniors, though anyone can linger in the Pavilions’ backyard gardens. The campus has been deemed a masterwork by the American Institute of Architecture. Tours leave daily from the Rotunda; don’t miss Edgar Allen Poe’s former room, encase by glass. Or you can easily tour the campus on your own. Walking these grounds is a timeless privilege, one best savored in morning’s first light, with the Lawn dewy and glistening under the rising sun, migratory birds twittering in the trees, and the mighty gong of the UVA bell rousing students to first classes. Don’t miss the eerie, gothic Chapel, tucked amid stately pines. It’s my favorite.

UVA student life (45,000 strong) revolves around The Corner, the row of coffee shops, bookstores, and bars along University Avenue. For a soundtrack to match, tune in to C’ville’s kick-ass radio station, Observatory Hill (aka O-hill), a hardscrabble 5-mile loop that bumps over rocks and tree stumps. The trail requires some sick climbing and tests your technical skills with tight turns, drop-offs, and slick patches of leaves.

When the James River is running, tubing is C’ville’s sport of choice - and the Coleman cooler is its semi-official mascot. James River Runners leads group tours down the deceptively-gentle-seeming, undulating waterway. Tubie-newbies, take note: When water gets whitecapped, butts in the air.

At the other end of the dumbbell, Charlottesville’s Downtown Mall broke smart-growth ground in the early 1990’s, transforming the blighted historic district into an eight-block-long, car-free esplanade. The Art Deco streetlamps, leafy oaks, and seating area are pretty, but frankly, the mall isn’t all that. The Charlottesville Chamber of Commerce fawns over it, but the mall has fallen victim to its own success: the look that it pioneered has become common across America, so the luster has dimmed a bit. Plus, it’s pricey—gotta pay those hefty rents. And I’m sorry, but that awkward band shell at the edge of the mall is just putrid.

Still, the mall gets big props for staying chain-store free, and remains the stomping ground of C’ville’s grad students, families, and young professionals (undergrads linger at the Corner). My favorite spot on the mall is the Charlottesville Ice Park a faux-60s throwback with bundled-up kids and adults gliding around a tiny rink, with local ads adorning the boards and cheap franks and fries at the snack bar. Ironically, the ice rink caused some controversy when it was built in the 1990s; some thought it would attract the ‘wrong element. Like who—Canadians?

Brush up on local history on a downtown walking tour with the local historical society, or follow the helpful signage to make your own. Glimpse the requisite southern statues of Robert E. Lee (nobly seated atop his show horse) and Stonewall Jackson (leaner, more dutiful, his steed in full stride). Linger a spell by the Lewis & Clark statue at the corner of Ridge and West Main Street. Check out Sacagawea, fawning submissively at Clark’s feat. Offensive? Demeaning? Yes, say intermittent protesters who show up to defend the woman who saved L&C’s asses again and again and again.

Indulge your inner explorer by traveling Charlottesville’s surrounding landscapes. Amateur oenologists can lose themselves along the Monticello Wine Trail, a circuitous grouping of lovely backroads that link two dozen local wineries, many of them smaller labels producing only a few thousand cases per year. King Family Vineyards pours a cherry-esque Cabernet franc in a setting with stellar Blue Ridge Mountain views; Hill Top Berry Farm & Winery has whimsical varietals including a tart cranberry wine and pear sangria.

The big attraction near Charlottesville is Monticello, Thomas Jefferson’s mountaintop retreat. This was no mere estate. Monticello was an empire. If you doubt this statement, flip a nickel and see what’s on the back. A work in progress for 40 years, Monticello today looks quite similar to the way it looked in Jefferson’s day, right down to his inventions placed throughout the house. Each room is uniquely shaped and done up with fineries, but my favorite spaces in Monticello are backstage. Like the basement wine and beer cellars, and the hidden staircases through which Jefferson’s servants (read: slaves) moved about the house.

Monticello extends way beyond the house itself: more than 5,000 acres comprise the surrounding plantation, Virginia’s first atop a mountain (instead of by a river). The grounds are truly regal, with orchards, vineyards, and groves formerly tended by slaves who worked in the ground’s smithery and carpenter’s shop, and occupied Mulberry Row (which is currently being excavated). The Thomas Jefferson Foundation (the current stewards of Monticello) don’t mind you strolling the grounds, or picnicking beside the gardens—the perfect spot to contemplate American history. Jefferson wasn’t alone among Virginian heads of state; Montpelier, outside Orange, housed Jefferson’s successor, James Madison; Ash Lawn-Highland, his protégé, James Monroe.

After hours, Charlottesville downright rocks. Never underestimate the impact Dave Matthews had on Charlottesville—all the more impressive when looking at the busker’s stage in the front window of dank, smoky Miller’s Restaurant, the downtown beer joint where he crooned for tips 20 years ago. His tour manager, Coren Capshaw, has grown downright Trump-like in these parts, with an entertainment empire that includes the king of the C’ville’s live-music scene, Starr Hill. It’s a winning formula: two music halls (downstairs cocktail lounge shows are free), a solid restaurant (order the cavatappi salad when heirloom tomatoes are in season), and a brewpub pouring award-winning Amber Ale and Dark Starr Stout.

Though I’m down with Starr Hill’s lineups—Yo La Tengo, Galactic, Southern Culture on the Skids—but truth be told, I prefer the scene (and underground noise-pop bands) at the Satellite Ballroom, tucked down an alley on University Avenue by the Corner. Smaller room, tighter sound, less patchouli, fewer schmucks gabbing over the bands. Another cool joint is Atomic Burrito, with its awesome pulled-pork burritos, and rotating bands booked by the night’s bartenders—you never know what you’re gonna get.

Charlottesville’s art gallery scene has mushroomed, with openings popular among scenesters, though much of what gets shown is so-so. One exception: Second Street Gallery, takes risks on talents like pervasive artist Gary Baseman and glass-installer Grahm Caldwell.

Charlottesville Restaurants: Eat Cheap

Hashbrown lovers, rejoice: C’ville’s best breakfast is back with the Blue Moon Diner ($), which reopened on Main Street in late 2006 after a two-year hiatus to ramp up their catering biz. They’ve broadened the menu, with items lie heirloom cuts of bacon and yellow beet salad. One bad holdover remains though: the slowest service this side of the Pecos. Don’t come if you’re in a rush.

Rush to grab a seat atContinental Divide ($$), a couple blocks from the Blue Moon. The sign says ‘Get in Here’, but should add ‘…Early, or Fat Chance Sitting Down, Suckers.’ Nevertheless, the eager and convivial pack this über-popular Southwestern eatery nightly, biding their time between seatings by knocking back boutique tequilas. The savviest show up at happy hour to snag one of a handful of booths, and dive into spicy quesadillas and veggie enchiladas, sniggering at the hordes vying hard for the barkeep’s attention, endlessly shuffling by the doorway watching the in-crowd nosh and quaff.

Don’t let the huge tree freak you out at the Twisted Branch Tea Bazaar ($), a non-descript second-floor walkup on the Downtown Mall. It’s living artwork that sets the stage for the room’s quirky niches, accented by burgundy sofas, gold-velvet sashes, teakwood tables, and beaming bodhisattvas gazing from above. Apple tobacco from communal hookahs and the occasional full-costumed barbarian lass lend a Nordic-Hindu-Turkish flavor to the place, which serves dozens of teas with names like designer drugs (White Monkey, Silver Needle) to mixed groups of the drowsy-eyed, who appear halfway to Nirvana. Not down with Yerba Mate? Grab a bottle of Boddington’s, pack the hookah and puff out. Want some air? Straight back to the rear deck.

The best pizza in Virginia may be a heady claim, but this Jersey native boy can stamp his approval on Crozet Pizza ($$), half an hour outside town in the tiny junction of the same name. This is the real deal: hand-tossed pizza baked to order (try the ‘hero,’ piled with hot peppers and sausage) in an ancient (well, decades-old) double burner stove. Founders Bob & Karen Crum converted a condemned building into Crozet in the 1970s; they handed down the business to daughter Colleen in 2004. She hasn’t missed a beat.

Charlottesville Restaurants: Eat Fancy

In the white-hot Belmont neighborhood (where Charlottesville’s hipsters wander the hilly, tree-lined streets pining for open-house signs), Mas ($$$) dishes up sweet Spanish tapas, without pricing regular schmoes (or starving students) too far out of el mercado. Mas’s 2002 arrival coincided with (triggered?) Belmont’s ascension. Today patrons come from across Albemarle County to hang on its open-air deck (arrive early) or pack the modern Euro-styled booths in a red-brick interior amid vintage black-and-white photos. The pulsating Latin music in the background is as varied as the menu’s offerings. Among the standouts: a melting brochetta d’atun (rare-grilled yellowfin with smoked tomato aioli); smoky-sharp chupa chups (quail legs wrapped in bacon, tossed with cocoa, paprika, and garlic); slippery boquerones con ajo (anchovies in olive oil, garlic, and lemon). I had a wood-fired fig, ham & mozzarella pizza that paired perfectly with the hot-smoked tomates asados. Individual dishes are reasonably prices, but the bill adds up fast—especially when you factor in the stellar Spanish varietals like Mazuela, a hearty red, and Xanello, a Catalonian sparkling white.

The hands-down coolest room in Charlottesville is the basement bistro C&O Restaurant ($$$), a Franco-American steakhouse hidden behind nondescript signage on Water Street. C&O has three spaces: Upstairs offers white-linen elegance; the dark mezzanine is seduction city. But the real action is downstairs in the rustic, cozy basement bistro, with oak stools and red-brick walls lined with libations that tinkle when the trains roll by. Dinner patrons couple Maker’s Mark and steak Chinoise (strikingly infused with ginger, tamari, and scallions), or beef tenderloin with seared foie gras, paired with a full-bodies Oregon pinot noir. Come 10pm, the in-crowd arrives for (surprisingly reasonable) drinks. It’s a bitch to score a table here, but play it cool with the host (and come as a pair, max), and you might get one of the handful of two-tops, a spot on the wall bench, or a couple of barstools. If you’re flexible, you’re in luck: aim for that sweet spot around 9:40 when the dinner set is finishing their crème brulée, but the long-haul boozing hasn’t yet begun. Entrées are served until 11pm; afterward, the late night menu kicks in (order the $10 cheese course). Food and mood aside, I love the C&O for its service—quick and attentive. When I tried to order the late-night artichoke plate at 10:45, our server gave it to me for the appetizer price, four bucks less. That’ll buy you another scotch in this joint.

Charlottesville Hotels: Budget

For the best access to life on the Corner, the Red Roof Inn ($) provides a good location; small, but clean rooms; and some of the best rates you’ll find ’round here. But its Byzantine parking setup forces you to navigate alleys and one-way streets to check in.

Which is why I prefer the Marriott Courtyard Charlottesville ($$), just a couple blocks down Main Street. A bit more upscale, the Marriott offers more space and amenities, including a lobby bar that actually draws interesting travelers. Rooms are framed like mini-suites, with a well-sized, glass worktable that easily handles my reams of paper, comfy loveseat (no Ikea cheapie), and pleasantly ribbed carpeting that subtly works my plantar fascia. Alas, the TVs don’t pivot toward the bed, a mild nuisance, yet not nearly as annoying as the unexplainable absence of hair conditioner. Who uses just shampoo? Sheesh.

A fun alternative to staying along the dumbbell is the English Inn ($), a quirky Swiss-chalet-shaped local property on US 29 to the north of town (just across from Whole Foods). A British sensibility and cheap rates are hallmarks of this hotel, which features high tea in the afternoons and a highly attentive staff. Rooms are crisply cleaned, if a bit staid looking. Suites have dual televisions, a nice plus. The indoor pool, gym, and sauna are bonuses at this price.

Hotels in Charlottesville: Splurge

For pure Southern decadence and charm, the Inn at Monticello ($$$) is the clear winner. Grand but still intimate, this bed and breakfast just outside town offers romantic respite without falling victim to the stuffiness you typically find at high-end B&Bs. Owners Bob and Carolyn set a laid-back atmosphere mirrored by the clientele, who mingle in the relaxing parlor. On my last visit I chatted with a young professional couple from Arlington who were planning their wedding in Charlottesville, and two mid-40s Asian couples raving about Monticello. Halfway between Jefferson’s masterworks, the white columned house has a big front porch and sits atop a small hill; there’s a rolling front yard, big flower beds, and cute benches here and there around the grounds, which beg exploring if only to inhale the crisply fragrant Piedmont air. Rooms are sizable and impeccably clean; all have solid queen beds, private fireplaces, and views of the forested grounds. Best of all is the quiet: unlike at some properties, here you can’t hear your neighbors, though one the cats who live here might wander into your room.

Like the rest of the Downtown Mall, the Omni Charlottesville ($$$) is a bit overpriced, but delivers a quality experience. Rooms are appointed with ultra-soft duvets and modern earth-tone furnishings. Rooms are on the small side, but if you get a top-floor room, views of the nearby Blue Ridge mountains can expand your sense of space.

Expect top-of-the-line treatment at the Boars Head Inn ($$$$), Charlottesville’s swankiest resort. Set on a 55-acres spread beside a tranquil lake, the restored 19th Century property resembles a countryside manor, and offers regal touches throughout—decadent artworks, 17 tennis courts, a spa, and nearby golf course. You’ll pay a lordly fee for the pleasure of staying here: Bring your checkbook.

Vacation Rentals

Vacation rentals can be tricky to navigate, but the payoff is huge. Whether you’re a budget traveler who can’t afford the double-whammy cost of hotels and restaurants, or a luxury traveler who wants seclusion and over-the-top grandeur, you’ll get more space and privacy for your money by booking a rental property. And you’ll have a kitchen too. Read our vacation rentals how-to guide to find our how, and where, to rent.