Top Ten Places to Drink Downtown

It’s no secret that Charlottesville likes to drink. Between TJ’s wine-loving ways and the boozy tomfoolery of the University, a Cville weekend without a craft cocktail and a glass of local wine is just… incomplete. Here’s a crawl of the top 10 places to press your belly to the bar on the Downtown Mall.


1. Whiskey Jar

Best for: dark liquor lovers, live music, outdoor space.

The chaps behind the bar at the Whiskey Jar can mix a mean cocktail, but you’re doing yourself a disservice if you skip the Virginia happy hour at this pub-style space. At half price, it’s the perfect way to discover a new favorite local distillation.


2. Miller’s Downtown

Best for: a pitcher, some pool, and some serious jazz

Miller’s might look small and unassuming from the outside, but its three floors and patio space have a lot more going on than just burgers and brews. A downtown institution, some of Charlottesville’s best Jazz shows happen on the first floor on Thursdays. The smoky third floor (the only indoor smoking in Charlottesville) does a hopping business in beer and pool games at nearly all hours.


3. Commonwealth Skybar

Best for: summer cocktails, watching the sunset, singles

Light, breezy cocktails, music, and a great opportunity to people-watch from their balcony overlooking the downtown mall– Skybar is a favorite destination for the post-work happy hour or the Saturday girl’s night.


4. Shebeen Pub & Braai

Best for: sports, easy access, ex-pats

Parking, an outdoor bar, and plenty of TVs– Shebeen is a solid spot to spend a few hours, knock back a few rounds, and hear a couple of accents. This South-African style pub is a favorite of Charlottesville’s expat community. Plus, outdoor karaoke.



Best for: groups, dancing, late night

Part pool hall, part dance club, Rapture is one of the few places on the mall where people still go to get wild. Bring your dancing shoes, remember to tip the DJ, and call an uber when the lights go up.


6. Alley Light

Best for: Date night, craft cocktails, special occasions

This speakeasy-style spot is a soft, lowlit space where the drinks are custom, comforting, and outrageously classy. Grab your Audrey Hepburn pearls or a tweed jacket, break out the 25 cent words, and sip the night away with a Doctor’s Orders.


7. Bebedero

Best for: Tequila, live music, date night

Any great night needs tequila, which means that any great downtown bar crawl needs Bebedero. Their list is long and seriously well selected, which means your biggest problem here will be deciding what to drink. Pro tip: make this an early stop- there are A LOT of stairs.


8. Draft Taproom

Best for: American sports, beer lovers, casual gatherings

Sixty taps, self-service, and wall-to-wall TVs. Draft is the spot to sample everything, pig out on fried snacks and Brussel sprouts, and trash talk the opposing team.


9. Tin Whistle

Best for: Outdoor late night, relaxing, no judgment

The Tin Whistle is unequivocally great for all seasons. The beer is cold, the whiskey is Irish and the service is fast and friendly. Their courtyard patio space is lush, green and shady, perfect for hot afternoons. The indoor space is cozy, warm, and winter-proof. Come here for maximum chill.


10. Livery Stable

Best for: Dive Vibes, local gossip, chilly nights

Livery Stable is an old-school, longstanding pub with a serious group of regulars. Never empty, they pull a solid beer and mix a quick, sweet shooter, but they’re not lagging in the cocktail craft, either. Open late, Livery is a reliable, quirky spot that’s always worth a visit.