If there is one thing I knew about Charlottesville, VA, it’s that it has a following. Anyone who’s ever visited or lived there is just obsessed with it! As it turns out, a lot of my friends went to UVA, and the second I mentioned that I was going to spend a few days in Charlottesville, I was met with jealous sighs and major nostalgia. And for good reason. Charlottesville is one of the sweetest, sleepy little towns I have visited. It has all the charms of the South, with beautiful views of the mountains. Add to that great food, history, and LOTS of wine tasting and you pretty much have the perfect weekend away. We stayed at The Oakhurst Inn, a quaint boutique hotel just steps away from UVA.
Two things to note if you plan a trip: Charlottesville is a little tricky to get to (we couldn’t fly direct) but once you are there it is so worth it. It’s also very close to Richmond, so you can always fly there and then drive the hour… it’s a really pretty drive! Also, dress casually. I brought my friend Deirdre. We both packed mostly dresses and skirts and felt very overdressed. Nearly everyone we met was in sweaters and/or fleeces. Noted for next time!
Dinner on Wednesday (our first night) was at Red Pump Kitchen, located on the Downtown Mall. The food was so good. We sprung for the tasting menu with wine pairings, which ended up being a very good decision. The restaurant is known for their homemade pastas and both Deirdre and I agreed that the tortellini (served with locally grown tomatoes + mushrooms and drizzled in truffle oil) was our favorite. We also had some great wines – the pairings were perfect!
After dinner, we visited Alley Light – a cool speakeasy style bar that also happened to have a great wine list (and yummy-sounding food too, as you’ll see by the sign!) It’s tucked away down a side street on the mall… so a bit tricky to find, but well worth it!
On Thursday morning, the first order of business was a tour of Monticello (Thomas Jefferson’s home!), which was absolutely beautiful.. especially as the leaves are just beginning to change color. If you go, I definitely recommend leaving early. The estate is huge – it takes a bit of time to park, secure your tickets, and take the shuttle bus up to take your tour. The property is breathtaking and it was fun getting to learn a bit more about Thomas Jefferson and his life.
The photo above may not look like anything special, but it’s really cool. Look at the structure of the windows – they actually fold up, accordion style!
After Monticello, we had a bit of time before lunch so we wandered around and did some shopping. Eloise (a few minutes away from the mall) was really cute – they stocked some of my favorite designers in a big, open space.
After lunch, we went wine tasting!
You may not necessarily think about wine when you think of Virginia, but maybe you should. The state boasts 252 wineries, 25 wine trails, and 10 winemaking regions. The top grapes from the area are Viognier + Cabernet.
We visited King Family Vineyards which was incredible. If you go, see if Tiernan can walk you through the wines. She was a wealth of information and so friendly! The vineyard is family owned and operated… super casual with beautiful views of the mountains. One cool thing if you go – on Sundays (between Memorial and mid-October), they have polo!
I’ve also heard wonderful things about Barboursville + Stinson. I’ve heard from multiple people that the Barboursville Octagon wine is particularly special. I wasn’t able to get my hands on any this trip but am planning on tracking down a bottle or two ASAP!
That evening, we attended an “Insta-Meet” at Pippin Hill with several local photographers + influencers.
Pippin Hill has to be one of the most beautiful places I’ve ever been. It’s set in the mountains, with the dreamiest views ever. I could not stop taking photos!!! We had fun meeting the area’s bloggers + Instagrammers, and drank some delicious wines. But really… these views! As beautiful as these photos are, they still don’t quite capture Pippin Hill’s magic. It needs to be experienced in person.
It came as no surprise that I’d love Pippin Hill as much as I did. The owners also own Red Pump Kitchen… and in Charleston they own The Zero George Hotel (as seen here, here, + here) and Cannon Green – two of my favorite spots!
After dinner, we went to MAS for tapas. A friend of mine (whose taste I respect) described MAS as the best meal of his life. So we kind of had to try it. It didn’t disappoint (although we way, way over-ordered!!) My personal favorites on the menu were the bacon-wrapped dates and the goat cheese artichoke spread. So good!!!! Also, their sangria is incredible and only $5. Nothing is $5 in New York!
The next day, we were up and at ’em to drive to Richmond. But before we left, we had to go to Bodo’s for bagels. So many of you said that we had to go there (and I also read this article), and I’m glad we did – our bagels were amazing. As an aside, Charlottesville has this whole culture around perfect sandwiches. People have very strong opinions on sandwiches there. Bodo’s is one of the more famous places, but Take-it-Away and Bellair Market (in a gas station) are both very popular! I myself am more of a salad girl, but as a foodie I really loved the enthusiasm!
Copy our trip:
Stay: Oakhurst Inn
Drink: Alley Light
Thank you to the state of Virginia for hosting us – we had an incredible visit!