How to Spend a Weekend in Charlottesville

my bachelorette at Pippin Hill!

Charlottesville… where do I even begin?! This charming town in the midst of the rolling Shenandoah mountains of Virginia is one of my very favorite spots to visit, and I’ve acquired quite a bit of knowledge about this beautiful town, and the surrounding areas, over the last few years. My sister, Bridgette, and her husband, Rob, lived there for two years while Rob was getting his MBA from the University of Virginia. I lived just two hours away in Washington, DC, so I spent many weekends over those years visiting their new home in Charlottesville. Even after they moved, I’ve been back to visit a handful of times, as I can’t stay way for long. I’ll share more details on this soon, but my bachelorette weekend (which lined up with my 30th birthday!) was spent in Cville with twenty of my best friends! It’s such a fun destination, filled with so many of my favorite activities: the rolling mountains/nature, gorgeous views, incredible wineries and vineyards, cute shops, amazing restaurants, and fun breweries and cideries. I’ve even planned three weddings in Charlottesville, where the wedding industry is alive and flourishing! Plus, it’s only about 3.5 hours away from Raleigh, making it the perfect spot for a weekend getaway.

Wineries you must visit:

  1. Pippin Hill – I think this is an obvious first choice, as I think it’s the most well known winery in the area (especially in the wedding industry!). And it lives up to the hype, for sure! You can’t bring outside food or picnics in, but their cheese and charcuterie boards and farm to table restaurant are extraordinary. So many seasonal, local, fresh ingredients are used, and Pippin Hill definitely has style and class to the max. They have beautiful tasting rooms, excellent knowledge of great wine, wonderfully trained sommeliers, and delicious wines. Some of the best wine I’ve had is from Pippin Hill, and I love that they emphasize many of the grapes grown on their property and that thrive in the mountains of Virginia. The sparkling rose is perfect to sip on the patio in the summertime, and I love their Petit Manseng, Cab Franc, and Meritage. The views of their vineyards and of the Blue Ridge Mountains are unparalled – be sure to catch a sunset, if you can! My sister lived just ten minutes from here, so you can bet we made frequent visits – and it was our first winery stop during my bachelorette weekend. Don’t miss this winery!
  2. Afton Mountain Vineyard – The vibe here is quite different from Pippin, but it’s a perennial favorite, too! The property is beautiful, the owners are incredibly welcoming and knowledgeable, and the wine is delicious. I still dream about the Gewurztraminer there! And I love that you can bring your own picnic with you: the best combination. Afton Mountain Vineyard and Veritas are just around the corner from one another, making it a super convenient  stop along your tour of the Virginia wineries
  3. Veritas – Veritas is really fun and a little busier than Afton Mountain, and I love how each winery varies from the next – they really have their own unique personality! I go to Veritas almost every time I’m in Charlottesville. They have a great tasting, good wines (their Viognier and Red Star are excellent!), and beautiful views and property. Sometimes they have live music, and I love bringing a picnic and enjoying it at Veritas – with a bottle of wine, of course!
  4. King Family Vineyards – The panoramic views of the mountains (you’re nestled in the valley at King Family) are stunning, and one of the best parts about King Family is the polo! Yes, they have regular polo matches throughtout the summer on Sundays, which seems like such a quintessentially Virginia thing to do: sip wine while watching the horses run by. When we went for a polo match one time, we brought a picnic spread, watched the polo match, and golf carts were driven by, selling bottles of wine right there. King Family has an excellent rose (Crose!), and I also am partial to their Roseland and Meritage.
  5. Blenheim Vineyards – This winery was founded by Dave Matthews (DMB got its start in Cville!), and I have even planned a wedding at this gorgeous property! Their vineyards are magnificent, the views take your breath away, and the restored buildings here are so beautiful. It’s no wonder I love Charlottesville wineries so very much. The tastings here at Blenheim are great, and you can’t go wrong with any of their wines.
my bachelorette weekend at Veritas Winery

Breweries and cideries to try:

  1. Blue Mountain Brewery – I’ve been to Blue Mountain Brewery many times (including my bachelorette weekend – we needed a departure from all the wine!), and it’s a perennial favorite! It’s just down the street from Afton Mountain Winery and Veritas, making it the perfect culmination of a day visiting wineries and brewries in the area. The mountain views are so beautiful, and they have ample, great outdoor and indoor seating (plus corn hole and market lights!). It always seems to be packed here, and for good reason! I like getting their flight of beers (I think you get about ten samples), and their food is really delicious and unique with a diverse menu.
  2. Devil’s Backbone Brewing Co. – This is another favorite brewery in the area, and it’s one we also visited during my bachelorette weekend as everyone was beginning to arrive to town! I love the property and design of the brewery (you kinda feel like you’ve been transported to another world!), and it’s really quite memorable. The food is delicious (thank goodness good beer and good food seem to go hand in hand around Cville), and their beers are great. I cannot remember which beer(s) I’ve had here, but I know I’ve loved all of them – and so did my friends!
  3. Bold Rock Cidery – I had never been to a cidery before visiting this one, and I’m sure glad I did! Instead of beer (brewery) or wine (winery), they brew cider at a cidery… and I think most anyone who has had hard cider knows of Bold Rock! We had so much fun here, and I went went this location newly opened. The property is beautiful, and, as expected, so are the views of a little river and the mountains. We had a free cider tasting (champagne cider! pear cider! peach cider!) and enjoyed every sip of it. I had no idea, at the time, that there were so many types of ciders out there, and I definitely learned a lot on the tour and during the tasting. It was a really fun departure from wineries and breweries, and I highly recommend trying a cidery – especially if anyone is gluten-free!


Delectable places to eat:

  1. Red Pump Kitchen – This was one of the best meals of my life – oh so memorable and delicious! Red Pump Kitchen, on the main pedestrian Mall in downtown Charlottesville, is owned by Lynn Easton, of Easton Events/Easton Porter Group/Pippin Hill/Zero George Hotel fame. Everything she does seems to turn to magic, and this restaurant is no exception. It’s at the top of my must-eat list in Charlottesville, and you’ll fall in love with it like I have! Their cocktails (and extensive wine list) are impressive, the ambiance and atmosphere are spot on, and the menu and food are amazing.
  2. Feast! – Feast! has received a lot of fame in recent years, and for good reason. It’s also on the Mall in downtown Charlottesville. It’s a cafe, food market, and foodie goft shop in one, and I could spend a happy hour or two browsing all of the goodies and sampling it all. Their sandwiches are perfect for a picnic to-go, and you can also load up on gourmet cheese, local treats, and all sorts of delectable eateries.
  3. Sweethaus – For a sweet treat, Sweethaus is my favorite spot for a cupcake or really anything else. It’s an adorable shop filled with everything sweet that you can imagine. I often use Sweethaus for my Charlottesville weddings, too!


More things you must do:

If wineries, breweries, cideries, and picnics haven’t kept you busy enough, here are some other beloved Charlottesville treasures to enjoy!

  1. Monticello – Thomas Jefferson’s stunning home is a must-visit when you’re in Charlottesville. The architecture, the grounds, the house, the history, the gardens – Thomas Jefferson is wildly popular in Cville and rightfully so. He pioneered so much in this area (and in our country), and this historic home, world heritage site, museum, and presidential library are not to be missed!
  2. stroll the Grounds at UVA – The University of Virginia is situated in the heart of Charlottesville, and you can’t miss it. Though, of course, I’m a diehard UNC alum and fan, the grounds, the lawn, and the rotunda are so pictureque and steeped in history and tradition. Grab a coffee and go for an early morning walk around campus and through town, and you won’t be disappointed. I’ve even planned a wedding in the UVA Chapel on campus!
  3. Carter Mountain Orchard – Carter Mountain is another can’t-miss spot in Cville, especially in the autumn (though it’s fabulous all throughout the year)! I think every resident of Charlottesville flocks here in the fall for apple picking, apple cider, their famous apple cider doughnuts, and pumpkins – I know I have a time or two. Since you’re at the top of the mountain, the panoramic views are incredible. It’s a quick trip from downtown, and there are a plethora of fun activities for those of all ages – orchards, fruit picking, a country store and bakery, live music, a peach festival in July, and wine/cider/beer tastings.
  4. Charlottesville farmers market – Charlottesville’s farmers market boasts on of the more robust markets I’ve been to. Every Saturday, it seems like every person in town makes sure to hit up this thriving, fun, diverse farmers market, and I’ve happily spent many hours wandering it. Fresh produce, meats, local foods, lemonade, plants, local artisans, baked goods, and so much more are teeming in this downtown market, and I think you’ll love wandering through it, too!

As you can see there are so many wonderful things to see, eat, and do when you’re in the beautiful mountains of Charlottesville, Virginia. Though it’s a fairly small town nestled in the heart of the Shenandoah Mountains, it’s alive and well with so much natural beauty, lots of history and traditions, UVA, and countless activities to choose from. I have loved every visit I’ve made to Charlottesville over the last five or so years, and I always can’t wait to come back again for more. I’m so happy it’s a quick drive away from Raleigh, and I’m excited to go there with Rob sometime soon! It’s the perfect getaway for a winery daytrip, a romantic weekend, a fun weekend with lots of friends, and the perfect destination for a bachelorette weekend! (I’ll be sharing all the details and a recap of my bachelorette weekend in Charlottesville very soon, so stay tuned!)

If you’ve been to Charlottesville, I’m intrigued to know what your very favorite spots are! Please share in the comments, as I’d love for the comment section to be a great resource and guide for anyone traveling to or planning a trip to Charlottesville! And if you haven’t been yet, what’s on the top of your must-do list?! I’d love to hear!

6 thoughts on “How to Spend a Weekend in Charlottesville

  1. Oh, Charlottesville! What a wonderful list you’ve put together. A few things I’d add:

    -Hiking at Humpback Rock
    -A scenic drive along the Blue Ridge Parkway
    -Easy hiking at Saunders-Monticello Trail
    -Foxfield horse races
    -Polo matches at King Family Vineyard on Sundays
    -UVA sports (especially baseball, tennis, and football)
    -Public viewing night at UVA’s McCormick Observatory
    -Barboursville Winery

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