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

• Charlottesville Travel Guide
• Pippin Hill Farm & Vineyards
• Afton Mountain Vineyards
• Jefferson Vineyards + A Few Charlottesville Restaurant Recs
• King Family Vineyards + A Few More Cville Restaurant Recs
• Merrie Mill Farm & Vineyards
• Early Mountain Vineyards & My New Favorite Restaurant in Charlottesville

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This past weekend, I went to Charlottesville and had THE BEST time. Man, how lucky am I that I got to spend four great years in this amazing college town? It will always have a special place in my heart and I would love to split my time in retirement between my two favorite places—Charlottesville and Charleston! Please circle back in about 35 years for an update.

My friends Emma, Jackie, and I planned this trip about a month prior, but we were definitely holding our breath since it was scheduled for after the inauguration and we didn’t know if that would impact things at all. Luckily, it all worked out—and truthfully, after the first three Wednesdays in January, it couldn’t have come at a better time. We left DC around 6pm on Friday and made it to town in time for a late dinner and to sneak in a few rounds of drinks before Virginia’s 10pm alcohol curfew.

The week before we left for Charlottesville, I was in quite a funk. For one, it was a really stop-and-go week with the MLK day holiday and inauguration. For another, the weather sucks, it gets dark early, and there’s not a ton in my daily life to look forward to right now. Working from home can be really isolating and feels a lot like Groundhog Day, so this little escape couldn’t have come at a better time. I also really enjoy weekend trips to Charlottesville because there’s no pressure—I’ve got no big attraction or food list to work through since I’ve done so much of it and we can really just go with the flow. On most trips, I find a nice balance between trying new-to-me places in Cville while mixing in the old favorite spots for nostalgic value. It’s also such an easy drive down from DC and you can get back home on Sunday afternoon in time to get ready for the week ahead. I hadn’t spent a weekend in Charlottesville since fall 2019, and this trip reminded me I need to spend more time down there.

Since I graduated in 2013, West Main Street has changed so much! There are so many more student apartments and restaurants/bars on that strip—it’s unrecognizable almost. One newish addition to this area is The Draftsman Hotel, which is where we stayed for the weekend. It’s a Marriott Autograph collection hotel and is almost right across the street from the Courtyard on the Corner, if you’re familiar—so the location is unbeatable. It’s easy to walk to Grounds or the Downtown Mall. We paid about $100/each for two nights and parking, which I thought was a great deal given the quality of the hotel. The lobby is so well-decorated, as are the rooms. The rooms are spacious, we could all spread out and get ready without bumping into each other, and super luxurious—we loved the sheets and the bathroom was stunning. I would love to return for another stay—and I also really want to check out the new Quirk Hotel in town.

Once we checked into the hotel, we walked down to The Whiskey Jar on the Downtown Mall. I hadn’t been in years, and wow, it was better than I remembered it! They had a lovely tent outside with heaters going and it was a great atmosphere. We started with the hush puppies and the biscuits, and then for my main I did the fried chicken sandwich with mac and cheese. It was so good—might be one of my favorite Charlottesville meals; I definitely won’t be waiting so long to go back! They’re also doing to-go cocktails that you can take and enjoy on the Downtown Mall—we had a round while we were waiting for a table.

After dinner, we hung out at the hotel and watched some Friends before calling it a night. That’s one of the big benefits of the alcohol curfew is that it really forces you get to bed at a reasonable hour!

Saturday during the day, we decided to go wine tasting! We picked up sandwiches from one of our go-to sandwich shops, Take It Away. Until recently, they just had a location on the Corner, but in December they opened a new location at the new Dairy Market right on Grady Avenue. Next time you’re in Charlottesville, definitely add the Dairy Market to your list! It’s such a cool food hall type place with stalls from some of my faves like Take It Away, Citizen Burger, and Moo Thru as well as a lot of new-to-me places. I definitely will be going back!

Once we acquired sandwiches, a bag of bread ends (they sell them for $0.50!), and house dressing, we made our way to King Family Vineyards, which I think is my favorite winery in town. They’ve got so much land that you don’t need a reservation since it’s easy to spread out and they also have several places you can sit indoors if you prefer. I also love that they allow you to bring outside food! We posted up for several hours and enjoyed a bottle of their new Verde vintage, which was a spritzer-like white, and a few bottles of sparkling—one brut and one rosé brut. My best friend Molly lives in town, so she was able to join us for sandwiches and wine and it was great to catch up with her, too.

We decided to round out the day by heading to The Virginian on the Corner. I love that place so much—when I walk in, I feel like I’m at home. We even decided to impulse-buy t-shirts so now I have some march from one of my favorite spots, hah!

For dinner on Saturday night, we splurged and went to 1799 at The Clifton. Located about 15 minutes from UVA, The Clifton was originally constructed in 1799 as a classic colonial-style home for Thomas Jefferson’s daughter and husband, Martha and Thomas Mann Randolph. I didn’t get a good shot of the house because it was really dark, but I’d love to go back during the day because it’s stunning! (I’m a sucker for a white house with a big front porch.)

I had never heard of The Clifton until recently, which makes sense as it was redesigned back in 2018 by the design team at Blackberry Farm—a place very high on my bucket list!—and given a new lease on life. It’s operated as a boutique inn since the mid-1980s and the rooms are stunning. One day I’d love to splurge and stay there!

As for dinner—it was really good. I do feel like it’s one of those restaurants that you go more for the experience and ambiance versus the food, because while it was good food, it didn’t blow me away by any means. (I much preferred the food at Whiskey Jar!) There’s a three-course prix fixe dinner, so I started with an arugula salad, then did the burger (as a surprise to no one!), and finished things off with a lemon tart. They also bring you warm fresh bread.

That all being said, I’m so glad we went—and I can’t wait to return for a drink at their stunning bar one day when the pandemic is behind us.

A trip to Charlottesville would not be complete without a bagel from Bodo’s, so we picked some up from the location on The Corner and then ate them on the steps of the Rotunda and took in the beauty of The Lawn. We also took a moment to take in UVA’s new Memorial to Enslaved Labors—definitely a sobering moment and a place I’d like to spend more time at.

Soon thereafter, we hit 29 North to come home—and let me tell you, I did not want to leave!

If you have any questions about Charlottesville or need recommendations for something, don’t hesitate to shoot me an email (katie@atouchofteal.com) or drop a comment below!