We’ve fallen in love with Charlottesville, Virginia. From the rolling hills of wine country to the buzzing city streets, this home to the University of Virginia is an eclectic mix of just the right stuff. A perfect way to spend an evening is to visit one of the many unique Charlottesville bars in downtown.

    Downtown Charlottesville

    Downtown is sprawling, and there are plenty of places to see, eat, and drink. But our favorite spot is the Charlottesville Historic Downtown Mall. Picture a tree-covered promenade with shops, restaurants, cafes, bars, street performers, and vendors. This character and ambiance are why four of the five Charlottesville bars we list are on the mall.

    downtown area of restaurants and bars

    If you drive, the area around the mall provides ample street and garage parking. But we recommend walking, riding the free trolley service, or catching a rideshare to keep things safe and easy. There are also plenty of hotels in and around downtown Charlottesville.

    If you’re looking for a unique experience, The Graduate Charlottesville hotel is a top choice. Popping up in college towns around the country, this school-themed hotel chain is both modern and whimsical. It’s located across the street from the University of Virginia and only a mile from the Downtown Mall. Oh, and it’s also home to two Charlottesville bars, including the first one on our list below!

    composition notebook that reads graduate, notepad, pencil and student id

    Heirloom Rooftop & Bar

    Located on the roof of The Graduate Charlottesville hotel, Heirloom offers views of the city and the mountains. It’s a restaurant and a bar, featuring local farm-fresh grub and craft cocktails to suit a variety of situations. Heirloom is a perfect place for pre-dinner drinks or a nightcap. The ambiance at sunset is pretty solid too.

    Recommendations: Jason had the mint julep because it seemed perfect for the setting. I opted for a local Viognier white wine to celebrate the state grape of Virginia. Both were solid choices!

    Heirloom website


    rooftop restaurant and bar with purple sky and hanging lights

    The Whiskey Jar

    We can’t rave about this place enough. Situated on the corner of the Downtown Mall, The Whiskey Jar is one of our favorites of all the Charlottesville bars. The food is delicious, fresh, and local. The atmosphere is fun and relaxed. And it lives up to its name with a killer whiskey selection.

    The Whiskey Jar also wins a shining star for having the widest Virginia-based selection of beer, wine, and liquor. They even hold a Virginia happy hour Monday-Friday with deals on local beverages. They seem to keep it in the local family as much as possible. In fact, the night we visited they hosted a launch party for a new Virginia brewery.

    Recommendations: Go local. And get whiskey! If you need dinner, this is our top choice for eats.

    The Whiskey Jar website


    cocktail with an orange peel next to a menu that reads the whiskey jar


    Another downtown Charlottesville bar with some Virginia beverage options is Miller’s. In addition to several local beers and cider on tap, they offer a shelf of Virginia whiskey and even had a local vodka (Jason’s choice).

    This three-story stop has a little bit of something for everyone. The first floor features live music and a vintage-looking bar. The second floor has a couple of small tables to help you escape to a quieter place with a friend or two. And the third floor has a smoky “dive bar” feel with pool tables and pinball machines.

    Recommendations: Try to catch a local band or musician on the small window-based stage. Miller’s is where Dave Matthews Band got its start – so you never know when you’ll be part of the next big thing to come out of Charlottesville!

    Miller’s website


    old, dark, wooden bar with lots of liquor bottles and empty barstools

    The Fitzroy

    You’ll feel the classic elegance as soon as you walk into The Fitzroy. With a black and white tiled floor, marble counters, and leather booths, we felt like Mad Men could have easily filmed a scene or two here. Though, we’ve never watched the show before, so not sure where that came from!

    The best part is that it’s relaxed. You can come in dressier attire or more casual wear and you’ll fit in either way. The bartenders wore Fitzroy t-shirts versus stuffy button downs. The vibe was drink fancy, but feel comfy!

    Recommendations: This is the place to get craft cocktails. They don’t feature local spirits, but the bartenders here can recommend and mix up a fun concoction for your sipping pleasure. It was our favorite mixology experience out of all the Charlottesville bars.

    The Fitzroy website


    orange cocktail on bar in front of white tiled wall with letter f and beer taps


    Located above Commonwealth Restaurant, this is another one of the rooftop bars in Charlottesville. It overlooks the Downtown Mall, providing ample opportunity to feel like you’re still part of the buzz on the street. To make things a little more comfortable, they also have ceiling fans and heaters lining the covered part of the bar.

    Recommendations: Check out Commonwealth Restaurant on the first floor too. We missed this opportunity but did sneak a peek on our way out of Skybar. It looked like an awesome place to grab a drink or a meal!

    Skybar website


    brown wooden bar patio with sign over the door that reads skybar

    Other Charlottesville Bars

    These are just some of the many awesome bars in Charlottesville. We couldn’t try them all, but we would if we could!

    Beer is also big in the Charlottesville area, so we’d love to go back and check out DRAFT Taproom and South Street Brewery.

    In addition to bars, the Charlottesville area boasts a variety of wineries, breweries, distilleries, and cideries. Check out our posts on the Nelson 151 trail and our favorite Virginia wineries from our 4-day tour!

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    We can’t thank Virginia.org enough for their support during our stay. They helped with accommodations, meals, and itinerary-planning for our four-day visit. But as always, our reviews are honest and genuine. We do not guarantee a positive review in return for assistance.



    Kate is Co-Founder and Content Creator at Intoxicating World, a travel blog featuring the history, culture, and booze of the world. She loves a good cabernet, won’t turn down a dirty vodka martini, and will usually order the Hefeweizen on tap.
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