Southern Belle in Training

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

May 14, 2019

Monticello Wine Trail: Chestnut Oak Vineyard

     A few weekends ago, my friend Liane came up from North Carolina to visit! On the Saturday that she was here, we were able to hit three wineries in one day- aka my perfect Charlottesville weekend. Today I'm recapping the first of three that we visited, Chestnut Oak Vineyard. 

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     Chestnut Oak Vineyard is located right off Route 20 North in Albemarle County, about halfway between Charlottesville and Barboursville. One of employees in the tasting room told me that they are one of the closest wineries on the Monticello Wine Trail from the Charlottesville city limits, so it's not hard or long at all to get there! It's easy to pair your visit to Chestnut Oak with some of the other wineries off of Routes 20 and 33, which is what Liane and I did. 

     I absolutely loved their tasting room! This is a smaller winery, but incredibly charming. There are two stunning wall art murals on the tasting room walls, and I was obsessed with how colorful and bright the tasting room was. The outside building is also very nice, and once their grapes are fully grown outside I can only imagine how beautiful Chestnut Oak Vineyard really is! (The plants had just started growing for the season in late April when we were there.) While Chestnut Oak isn't big enough yet to host weddings, they have just recently started hosting smaller private events and large group tastings at their facility, and I could see this being a great destination for something like work event or birthday party!

     I really liked the wines at Chestnut Oak! Liane and I did a tasting, and it had a nice mix of reds and whites. They also provided some little snacks to munch on with tastings, which is always appreciated! My favorite wine I tried was the Alba, which is is made similarly to their Viognier. I honestly enjoyed all of the wines though, even the reds. 

    Chestnut Oak was our first stop that day, and then we continued up Route 20 to visit Barboursville Vineyard (the largest one in this area of the Monticello Wine Trail- review coming next week on the blog!), and Reynard-Florence Winery, which I have been to before and is also a great smaller winery. 

    I think I can definitely add Chestnut Oak to my list of favorite smaller wineries on the Monticello Wine Trail! I definitely hope to go back this summer.

     Check out all of my past Monticello Wine Trail winery reviews on this page- just scroll down to where it says "Virginia Wineries."

     God Bless,

     xoxo Annaliese 



  1. Looks like beautiful spot. Love your dress - it's perfect for spring! Nipa

  2. Oh my gosh- this is such a fun spot! I loved your outfit and you are just glowing girl! I need to visit a winery soon!!

  3. Omg i cannot get over how beautiful the scenery is! And it sounds fun!

  4. I live in Richmond and love road tripping to Charlottesville for wine tours w girlfriends

  5. This looks like such a fun day! I love a good wine tour.

  6. Absolutely love your dress. I love wineries but never seen one so colorful and bright. I would definitely visit!

  7. What a fun girls’ day. Love the cozy look of this winery. And your spring dresses and hats are lovely!

  8. You look beautiful! This winery is lovely, I love the art on their walls and your dress is so dreamy. Your dress went perfectly with the murals and this maxi is perfect for wine tasting! I wish Alabama had closer wineries.

  9. Beautiful photography. Love your pretty dress :)


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