Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

February 6, 2020

5 Charlottesville Wineries to Visit in Winter.

     I've become quite the fan of visiting local wineries since I moved to Virginia a couple years ago! While I do think my absolute favorite time of year to visit wineries is in the summer (I love seeing all the grapes growing on the vines!), they are still fun to visit year round. Checking out Charlottesville area wineries in winter also has some advantages- namely the fact that it's not tourist season so they're not nearly as busy in the colder months! Winery visits from December-March are more of a cozy and intimate experience, which is still fun and special in a different way.

     Today I'm sharing five local wineries that I think are more ideal to check out in the winter months! I'm highlighting these five wineries for two main reasons: 1) they're all easy to drive to. Some wineries on the Monticello Wine trail are definitely off the beaten path (think long and winding dirt roads with no cell service), and winter just isn't the best season to attempt getting to some of those. The ones I'm featuring today are all located just off main roads and are easily accessible in all seasons. 2) They all have good sized indoor tasting rooms. On days when the weather is too cold to be outside, you don't want to be cooped up in a tiny tasting room at a winery that mainly has outdoor seating. These five all have fairly large and very cozy indoor spaces for guests to enjoy!

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5 Charlottesville Area Wineries to Visit in Winter:
     1. Veritas Vineyard and Winery {151 Veritas Lane, Afton VA} - This is where these photos were taken! My friend Emily is actually the Events Manager there, and she gets to bring the beautiful weddings that Veritas hosts to life. (And shout-out to Emily for taking the photos in today's post!) Veritas is definitely one of the larger and more established wineries on the Monticello Wine Trail. They have a diverse array of great wines and the views from the property are stunning, but because of this it does tend to get crowded there during the warmer months. Winter is truly an idea time to visit Veritas! The decor of the tasting room also feels very winter appropriate to me- it's filled with leather furniture and a roaring fireplace to warm you up while enjoying your winter wine tastings. 
     2. Pippin Hill Winery {5022 Plank Road, North Garden VA} - Pippin Hill might be one of the best known wineries not online in the Charlottesville area, but in the entire Southeast! Their cuisine is actually about as well known (if not moreso) than their wines, and they have some of the most beautiful views of any winery I've ever seen. Fun fact: Pippin Hill was also the site for this Gal Meets Glam dress shoot last year! Like Veritas, Pippin Hill tends to get really busy in the warmer months. Winter is a much quieter time to experience the beauty of this winery. They also have some indoor seats that face out towards the mountains, so you can still enjoy the amazing views while warming up indoors.

     3. King Family Vineyards {6550 Roseland Farm, Crozet VA} - My favorite larger winery on the Monticello Wine Trail! I love King Family Vineyards. (One of my all-time favorite blog posts of 2019 was shot here!) My favorite thing about King is that they do polo matches that are open to the public every Sunday (weather permitting) in the spring and summer! Winter obviously isn't polo season, but it's still a great time to visit King Family. They have a beautiful tasting room that's full of windows and natural light. It has ample seating and some large tables to accommodate bigger groups as well- I was actually here last month for a friend's birthday and this was the perfect winery to host that big of a group in January! 

     4. Chestnut Oak Winery {5050 Stony Point Road, Barboursville VA} - This was one of the most fun boutique winery discoveries I made in 2019! Chestnut Oak is located right off Route 20. I really liked their wines, and they have an adorable little tasting room that features the most beautiful murals! I think that sipping wine in their charming and artsy tasting room on a cold winter day would be an easy way to cheer up in the cold. 

     5. Glass House Winery {5898 Free Union Road, Free Union VA} - My favorite smaller winery on the Monticello Wine Trail! This is the only one out of these five that I haven't written a dedicated blog post review for yet- that will change soon I promise because I have absolutely fallen in love with this winery. In fact, I've been here more times this winter than I've been to any other local winery! Glass House is a boutique winery that has the most luscious tropical greenhouse as its tasting room. Talk about a way to beat the winter blues right?! Their Signora wine is my favorite Virginia wine of all time- and that's a high compliment! (The other wines are great as well.) Glass House also employs a chocolatier that makes gourmet chocolates to compliment all their wines. And they have ample outdoor seating as well by a beautiful pond- so if you happen to visit on a warm day you don't have to stay in the greenhouse. 

     Charlottesville locals- do you have any other winter favorite wineries I should add to the list? And if you're not from my area, do you have any local wineries near where you live that are perfect to visit year round?

     God Bless,

     xoxo Annaliese 



  1. I love wine, hope to go visit there one day! You look beautiful, dear, and your hair is nice. You look like a beautiful fairy tale princess!


  2. I love your outfit, it's so cute! I've never even been to any wineries before, I need to rectify that for sure! xo

  3. I adore your dress! These all sound lovely. We don't have any local wineries that are close. They're all at least an hour away. Nashville has an awesome one that we love to visit. I'm counting down the days until I can sip some wine again.

  4. Hi Annaliese,
    I love your post about Charlottesville Area Wineries to Visit in Winter. I love your outfit you are looking simply gorgeous.

    Cafe in Charlottesville VA

  5. Love love love this! I’d add Barboursville to this. Love Pippin Hill and have been meaning to check out Veritas ��. Thanks for the recommendation!



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