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!
Outfit Details: Burberry Trench // Rebecca Taylor Dress // Sole Society Shoes
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
Eat: Red Pump Kitchen // MAS // Bodo’s Bagels
Drink: Alley Light
Shop: Eloise (we also heard amazing things about Scarpa, but didn’t have a chance to visit.
Wine Tasting: King Family Vineyards // Barboursville Vineyard // Stinson Vineyard // Pippin Hill Farm
Thank you to the state of Virginia for hosting us – we had an incredible visit!
Pippin Hill Farm looks incredible…if they’re also behind Zero George then it’s no surprise it would be! Looks like such a fun trip.
Yessss! I know you love Zero George as much as I do! Definitely get to Pippin Hill if you can!!!
Pippin Hill Farm looks so dreamy like the perfect wedding reception place!
I hope to visit one day! I did know they have plenty of wineries because they host a Wine Country Half Marathon!
I hope you do visit!! It’s so special!
I’m obsessed with that dress! Looks great on you!
Also, I went to school in Northern Virginia so I knew a ton of people that were from Charlottesville and you’re right….they’re OBSESSED with their town! It looks so cute though!
Pink Champagne Problems
Thank you Dana!
Yes, it’s so funny. I guess I can’t relate as I’m not very passionate about my own college town (Waltham, MA – outside Boston) but I can see why everyone is so obsessed – it’s beautiful!!
Oh my, everything looks so magical and picturesque!!! Beautiful photo diary!
Thanks so much, Natali! Hope you had a wonderful weekend. xx
I’m glad you enjoyed your time in Charlottesville. I loved living there, and agree that everyone dresses very casually. I still wore a lot of dresses and skirts, but said goodbye to my heels for a few years.
Thank you Katie! Yep, we definitely didn’t need to pack our heels! Ha!
You hit all the best places (extra glad you found Alley Light). If I could add one place on, it’d be Bluegrass Grill for breakfast/brunch. Hope you snuck a peek of UVA grounds/the lawn as well.
Yay! So glad you approve. We DID get a peek at UVA – it’s beautiful. And thank you for the tip on Bluegrass… I guess we’ll just have to go back! 😉
The pictures are gorgeous! What a nice little location for a weekend away 🙂
Thank you, Marta! It really was the perfect little weekend escape!!
Just a wee bit overdressed for Bodo’s Bagels… Such a fu trip! Having a hard time with reality today, thank you for bringing me!!!!
Just a touch. I miss it. Let’s go back.
Love! Looks like you had the best time!
Thanks Jenn! We had a blast! xo
Looks very cute and very cozy 🙂 I’ve never heard of this place, actually!
Oh really!? It’s beautiful!! I hope you can visit some time. 🙂
Oh how lovely! You know I’ll be consulting this again before my next visit to see my sister at UVA Law.
Aw, good!!!! And ask your sis for her fave spots!!!
Wow, what a fun trip! I didn’t realize there were so many great spots in Charlottesville! I love all the wineries and local spots! Hope you had fun!!
Thank you Sarah!! There are so many fantastic spots – already dreaming about my next trip back!
You can fly direct in to Charlottesville-Albemarle (CHO).
Thanks for the tip!
Wine tasting and a loaded bagel?? This sounds like the perfect trip!
Truly! Two of my favorite things!!!