Editor’s Note — if you’re looking for additional Charlottesville recommendations, here are some other posts to check out: 

• Charlottesville Travel Guide
• A Girls’ Weekend in Charlottesville
• Pippin Hill Farm & Vineyards
• Afton Mountain Vineyards
• Jefferson Vineyards + A Few Charlottesville Restaurant Recs
• Merrie Mill Farm & Vineyards
• Early Mountain Vineyards & My New Favorite Restaurant in Charlottesville

While I originally wrote this post in 2019, I’ve gone back since then and added some photos I took at King Family in 2020 + 2021. After continuing to explore Charlottesville wineries, King Family has been solidified as my favorite. I love their wine, they allow you to bring outside food, and because they have so much space, you never have to worry about finding a spot. Pippin Hill and Merrie Mill are at the top of my list, too—but if I had to crown a favorite, it would be King Family!

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Hello + hope everyone is having a great Monday! I have the day off work—it’s the first time I’ve ever gotten Columbus Day off, and it couldn’t come at a better time as I worked all weekend at New York City Wine & Food Festival with my day job. I came back last night and have been enjoying a lazy day in DC. The weather is glorious, so I went on a nice long walk and treated myself to a McFlurry—something I haven’t done in years!

Today though I wanted to throw it back to a few weekends ago when I went to Charlottesville with my best friend, Lauren, to visit our best friend, Molly, who lives in town. We’ve got our visits down to a wonderful routine now, and pretty much always spend Saturday afternoon wine tasting. This go-around we went to King Family Vineyards, which has been a favorite of ours since college. It’s about a 30-minute drive from downtown Charlottesville—and it’s an easy drive. They allow outside food, so we stopped at The Market at Preston Avenue, which, hot tip, has the same menu as our beloved Bellair Market without the lines. When we arrived, we decided to do a tasting, which is $10. You don’t need a reservation, and when we walked in, the hostess helped us find a tasting bar with space.

We had a perfect spot at the bar overlooking King Family’s beautiful lawn and the rolling Blue Ridge Mountains!

After we finished our tasting, we bought a bottle of our favorite wine to share—Crosé Rosé. It’s by far their most popular wine, and they told us they normally sell out by the end of September, so we were lucky to still be enjoying it. We snagged a picnic table underneath their covered back patio, and it turned out to be a very good spot since it started down pouring about an hour later!

One thing I’ve always wanted to do at King Family, but never had the chance to do yet is King Family Polo! On Sundays from Memorial Day through early October, there are polo matches at 1pm that are free and open to the public. And, of course, you can enjoy King Family wine while watching the match.

On this last trip to Charlottesville, my friends helped me cross C&O Restaurant off my bucket list! Since C&O is located just off the Downtown Mall, we grabbed a pre-dinner drink at our favorite place on the Mall, The Fitzroy, which has become one of our favorite post-college watering holes in Charlottesville. It’s got a really fun atmosphere with dimmed lights and beautiful decor, and several large TVs in case you want to catch a game. I enjoy eating there, too—they’ve got a great burger!

C&O Restaurant is known as one of the best restaurants in town and its located in a historic building across the street from the old Chesapeake & Ohio train station. We were seated upstairs in a room with four or five other tables. The bread they bring is amazing, and then I started with a caesar-inspired salad. The menu is constantly changing based on what’s in season, so every time you go, it could be a little something different. For my entree, I opted for the steak chinoise, which was delicious. Overall, I’m glad we went, but I thought the vibe was a bit stuffy and our waitress wasn’t the friendliest. In the future, I might opt for the more approachable late night menu and sit at the bar!

After our delicious meal at C&O, we went to our favorite spot for a nightcap—Southern Crescent Galley and Bar, which is a New Orleans themed bar I’ve written about here a few times before. We love their back patio—and they make one of my favorite margaritas ever!