I am a frequent visitor to Charlottesville, VA, because my best friend lives there and I am headed there this weekend in fact. I can likely lend some advice and provide some information about Cville -- mostly food and drink. Craft beer lovers, foodies, late night eaters, and local music lovers will be very happy. The restaurant scene for foodies is probably the best you will find in a small college town with dozens of 4 star and above. There are more restaurants in Cville per capita than anywhere else in the US. Late night food is the best in any town or city in the country and I eat a lot of late night food after drinking while traveling to soak up the booze and ease the hangover. Craft beer isn't the best, but its good and for a town this size is better than you'd expect.
Nightlife:
There are three main areas for nightlife in Cville. First is the downtown pedestrian mall filled with bars and restaurants, mostly semi upscale places. Second is Main Street, which is filled with unique shops, but also has some bars and restaurants. Third is "The Corner", which is a bunch of college bars (maybe 10-15) packed into a very small area of a block and a half. Once I turned 35, I stopped going to the corner bars and tend to hang out on the downtown mall.
Craft beer spots:
Beerrun is a world class bottle shop and bar in a strip mall kind of about 2 miles from downtown mall or Main Street. Food there is decent, but there are lots better places for food in Cville. They have about 15 taps all craft and usually something really cool on tap. Tons of bottles in floor to ceiling coolers at discounted prices to go, but they typically charge a small fee to drink bottles there since they charge retail not bar prices for those bottles. Back room has a bunch of Belgians in bottles and Saturday night is Belgian beer night with no capping fee to drink them there.
World of Beer is 2nd best for craft beer/arguably first, is on Main St. and has 500 bottles and 50+ taps of pretty good beer. Its a chain so if you've been to one, you know what to expect. Typically something special on tap and a lot of above average beers.
Whiskey Jar is 3rd best for craft beer and is on the downtown mall. Probably 25 taps at least 5 of which will be darn good, tons of whisky brands including some special stuff. Usually good music on Saturday nights.
Citizen Burger Bar on the downtown mall has a good craft beer list and excellent burgers.
Sedona Taphouse is a 10 minute drive from downtown, but has 50+ taps many of them good.
Timberwood Grill is a good 15 minute drive from downtown, but a decent tap list of 45
Mellow Mushroom is on the corner and has very good beer.
Court Square Tavern I believe still exists from Jefferson's days and is just off the downtown mall. Special selection of bottles, many rare beers, but its in a cellar and is dark and not a real energetic or boisterous drinking spot.
Horse and Hound is on Main Street and has about 10 taps of imports from Europe. Good beer, good English pub food.
Wild Wing Café is on Main Street and has decent beer and tons of TVs for game watching.
BW3 is in a strip mall a 5 minute drive from downtown and less decent beer, still tons of TVs.
There is even an indoor hockey/skating rink on the downtown mall that has 4 taps of decent craft beer.
There are lots of breweries in and around Cville, several of them pretty good. Champion is just outside of downtown a short walk away and makes decent beer and a pretty good IPA. Three Notch'd is just outside of downtown and a very short cab ride and they make good beer. South Street Brewery has been bought by Blue Mountain Brewery and is now making great beer and also hosts guest beers from Blue Mountain and others. Blue Mountain's barrelhouse series of beers is outstanding (Spooky in particular is amazing and I've brought bottles up to NY and people were dying for more). Civilian is on Main Street but a warning, there beer just flat out isn't good but its getting a bit better now with a new brewer.
Hard Liquor(Whiskey and cocktail) spots:
Whiskey Jar on the downtown mall has a great selection of whiskey and bourbon. Laid back hipster crowd.
Millers is on the downtown mall. Dave Matthews played their once a week before hitting it big. Great whiskey and bourbon selection and good live music on weekends. Laid back townie/hipster crowd.
Commonwealth Restaurant and Skybar is on the downtown mall and has an awesome rooftop bar with good cocktails. This is where the players and divas go, but the rooftop is pretty cool.
Blue light Grill is on the downtown mall and has great cocktails and a raw bar with good oysters if you are early. Yuppie players and divas.
Maya is on Main Street and has good cocktails, decent craft beer and good high end food. Cool, laid back crowd.
Zocalo on the downtown mall has good margaritas and other good cocktails. Yuppies and packs of girls out on the town for the night.
Bang tapas restaurant, just off the downtown mall on South St., has very good cocktails. More a restaurant with good cocktails than a bar.
High end food:
The Ivy Inn -- most upscale, most expensive, best food. Classics on white linen
Fleurie -- high end French, very good, very expensive
Alley Light -- excellent new American/French, great for seafood.
Tavola -- high end Italian, not a spaghetti and meatballs place. Awesome scallops.
Orzo -- Italian , Mediterranean high end
The Shebeen -- African upscale
Maya -- upscale southern comfort food.
Whiskey Jar -- similar to Maya
Commonwealth -- new American
Zocalo -- new american
Mas -- tapas
Public is on Main St. and an oyster and raw bar along with a very good seafood restaurant that has a very good selection of oysters sold per piece.
Rocksalt -- Another great oyster bar and seafood place.
Citizen burger bar is upscale somewhat expensive but very good burgers
Cheap but great food:
Ace BBQ: Just off the downtown mall maybe 1/4 mile away. Their smoked meats are incredible, generally served on buiscuits as a sandwich.
Mel's Diner -- On Main St. -- good fried chicken, greasy spoon.
Wayside -- incredible fried chicken to go from a gas station
The Corner --not at the corner, its on Cherry St. in a bad part of town, but the best burger in Cville. Get it to go.
La Michoacana--authentic Mexican street tacos, like tongue, but also normal stuff like beef and carnitas.
Al Carbon -- Peruvian rotisserie chicken. So moist, great and very healthy.
Late night food:
Marco & Luca -- on the corner. open til 3 or 4am. Chinese pork dumplings that are awesome for like $4/order. I literally can eat 75. They only sell those or a noodle dish and all to go.
Littlejohns- on the corner. Awesome sandwiches, open 24 hours.
The White Spot -- on the corner. greasy Burgers and fries, but the "gusburger" is awesome with a fried egg on top.
Benny DeLuca's -- on Main St. NY style pizza place.
Occasional foodtruck on the downtown mall.
Plenty of Wafflehouses, Ihops and Denny's open 24 hours.
