Downtown Charlottesville, Virginia
Nestled up next to the majestic Blue Ridge Mountains, Charlottesville is far more than a college town and home of the Dave Matthews Band. While we can't stop you from whistling "Crash into Me" while you stroll around town, we can help you get the most out of a visit.
From deep-seated history and world-class wines to of-the-moment New American cuisine, this Southern city in the mountains is a perfect place to spend a weekend.
Where to eat and drink
You'll find just about any genre of food you desire in Charlottesville — even world-class Sichuan fare.
For a simple breakfast, head to Cafe Marie Bette for classic French pastries, egg-topped tartines and coffee. Or if you'd prefer a more rib-sticking meal, seek out the Ol' Dirty sandwich from Brian Ashworth's Ace Biscuit and Barbecue. The towering biscuit dish comes layered with fried chicken, sausage gravy, pickles and smoked pimento cheese. Of course, you can also choose a less caloric build-your-own biscuit breakfast, or head in for lunch for pulled pork, ribs and/or brisket.
Another lunch option — especially if you'd like that lunch to come with a beer (vacation!) — is Beer Run, a craft beer emporium, bar and casual restaurant. There, you'll find everything from sandwiches to burgers and wings, plus breakfast tacos on Saturdays and brunch on Sundays. And plenty of beer, of course.
Dinnertime brings even more decisions to be made. If you're craving pizza, head to Lampo for true Neapolitan pies made in a wood oven, an all-Italian wine list and unique Italian-inspired cocktails. Pizzas come topped with either ultra-traditional ingredients or local produce from the region's many sustainable farms. For a trendier, New American dinner, visit Oakhart Social for vegetable focused shared plates made with all the ingredients us millennials are always talking about. (Octopus! Shishito peppers! Za'atar! Castleveltrano olives!) Cocktails are big and bold and the communal seating on the patio is dog-friendly.
At the truly farm-to-table Back 40, you'll find more New American cuisine, but with a pared down menu. Just about everything served at Back 40 was grown or raised at the owners' sustainability-minded Timber Creek Farm, including the steak, a highlight of the menu. If you'd rather cook yourself, you can also stop into the connected market during the day for much of the meat and produce grown on the farm.
For more upscale fine dining, head to The Alley Light, a 2015 James Beard semifinalist for best new restaurant. Its menu is French-influenced (definitely a popular choice in Charlottesville) and dining is meant to be a communal, shared experience. The roasted bone marrow with escargots is a can't-miss, as is the seafood charcuterie board.
Or do the total opposite and dig into some excellent Peruvian rotisserie chicken at Al Carbon. The restaurant, located in a strip mall on 29N, is a favorite among locals, and it is known to also make mean cemitas. Another local favorite? Peter Chang's China Grill, which is, when he makes an appearance, home to one of the best (and most elusive) Sichuan chefs in the country. Peter Chang is known for his fiery cooking, and you'll still dine just fine at his eponymous restaurant even if he's not around. Try the dry fried eggplant, scallion bubble pancake with curry sauce and anything labeled "hot and numbing" on the menu.
Finally, if you're up for a bit of a drive, head to The Shack, located about 45 minutes west in Staunton. Chef Ian Boden has twice been named a Beard semifinalist for the region, the restaurant was named a Best New Restaurant by Southern Living, and it consistently is included in Eater's Essential 38 restaurants. The Shack serves an eclectic mash-up Southern, Appalachian and Eastern European dishes; on the menu you'll find everything from grilled pork loin with sweet potato grits to black pepper spaghetti with house-made ricotta miso and scallop bottarga. It's sure to be a memorable dining experience, no matter your order.
Where to play
While there is plenty of hiking to do and history to explore, our favorite thing to do on a Charlottesville trip is to tour wineries. Its surrounding region is home to dozens of acclaimed wineries, both large and small, and it is easy to tour many of them over the course of a day. Before you head out, stock up on snacks and other goodies at Feast, in Main Street Market. The store specializes in world-class cheese, but you can also find excellent charcuterie, sandwiches and prepared salads to pack into a picnic.
If the name of the game is volume (of wineries, not necessarily wine), spend some time planning with the Monticello Wine Trail. The wine trail boasts a collection of 33 member wineries, and you can pick and choose and plot a tour path directly on its website. All of the wineries included on the trail are located in the Monticello American Viticultural Area (AVA), which was the first established AVA in Virginia, and are all within 25 miles of Charlottesville. Places to visit include the famed Stinson Vineyards, which specializes in small lot wines with a distinct French influence, family-owned Veritas Vineyards, and Dave Matthews-owned Blenheim Vineyards.
For those looking to go off the beaten path, we recommend heading out to Ankida Ridge for best-in-class, unique pinot noir. Its acclaimed wines are made with little intervention and a strong sense of terroir. We recommend calling ahead before you visit; the winery has limited hours.
Where to stay
Beyond the obvious Airbnb and VRBO listings, there are quite a few unique inns, hotels and estates at which to stay if you're willing to throw down a little extra money. The Oakhurst Inn, located steps from UVA's Scott Stadium, is a charming and historic place to stay, with 27 unique rooms that are slightly more low-key than the other lodgings on this list. Another smaller, but even more luxurious, inn is the Dinsmore House, a fully refurbished 19th century home with nine guest rooms. Located in the heart of Main Street, the house was originally build in 1822 by James Dinsmore, Thomas Jefferson's master builder. If you're really looking to splurge, book a room at The Clifton, a luxury hotel and venue on 100 acres east of town. You can choose from a selection of rooms and suites in the Manor House and converted stables, private cottages, or even an entire farmhouse on the property, and all guests are given access to the downtown Common House social club.
Photo (hero): Bob Mical/Flickr (license)
Photo (Ol' Dirty Biscuit): Jimmy Emerson, DVM/Flickr (license)
Photo (pork belly): Oakhart Social/Facebook
Photo (tartare): The Alley Light/Facebook
Photo (cabbage): The Shack/Facebook
Photo (cheese): Feast/Facebook
Photo (vineyard): Monticello Wine Trail/Facebook
Photo (Oakhurst Inn): Oakhurst Inn/Facebook