Joe and I got to spend a romantic winter weekend in Charlottesville, VA for Valentine’s Day this year. As you guys know, we love to travel and it was nice to hop in the car for a little getaway. My travel style consists of checking out entertaining spots and eating really good food.

I’ll cover what you should know about Charlottesville, VA, what to pack for a winter weekend, where to stay, things to do, and where to eat. Read on for further details and stick to the end for an itinerary you can use for your very own weekend in Charlottesville, VA.

About Charlottesville, VA

What is Charlottesville, VA known for?

Charlottesville, VA is most known for being the home of two presidents, Thomas Jefferson and James Monroe. Thomas Jefferson found The University of Virginia and his home, Monticello, is a well-known spot that attracts tourists every year.

Why is Virginia known for lovers?

We decided to go to the state known for lovers for Valentine’s Day. I was curious about how VA had claimed that title and found out that Virginia had a court ruling in 1967 that legalized interracial marriage in the United States. What a beautiful story, right?!

Where To Stay

The Graduate Hotel

Shop my outfit : Moss Green Jumpsuit

We stayed at The Graduate Hotel, which was located right in downtown Charlottesville, VA, right across from The Grounds and I was extremely happy with the hotel as well as our location. It was easy to walk to spots to get breakfast and we felt extremely safe.

We took advantage of their friendly valet service which ended up being a great convenience especially with the colder weather. It made a big difference to have our car waiting for us right in front of our hotel. The Graduate Hotel has a rooftop and a restaurant which was closed during our stay due to COVID.

Our room was spacious and I was so happy to be able to bring Banjo along with us!

Things To Do – Winter Weekend in Charlottesville, VA

Admittedly, we did not visit during Charlottesville, VA’s peak season. They are well known for their spring and fall. With that being said, there were still quite a number of activities to take advantage of. If you do plan a winter weekend in Charlottesville, VA, I would make sure to have back-up plans. We did run into a number of businesses being closed due to the weather.

Monticello Wine Trail

Shop my outfit: Cream Midi Dress, Leather Leggings, Black Wide-Brim Hat

Monticello Wine Trail – The Monticello Wine Trail has more than 30 beautiful wineries. I would highly suggest checking out the trail at this link, to plan your visit. The Monticello Wine Trail was inspired by Thomas Jefferson’s vision of grape growing and wine-making. Making plans for a wine tasting is almost a necessity!

We visited the following wineries:

— Pippen Hill Farm & Vineyards – 5022 Plank Rd. North Garden, VA 22959

This vineyard came highly recommended but unfortunately was closed on the day we were on the Monticello wine trail due to weather. I hope to be able to make it there soon!

— Veritas – 151 Veritas Lane Afton, VA 22920

We enjoyed a tasting and a flatbread here. I can easily see this vineyard being absolutely stunning with warmer weather! They fill up quickly on the weekends.

— King Family Vineyards – 6550 Roseland Farm Crozet, Virginia 22932

They offer lots of seating options outdoors and indoors. We were able to snag a seat inside to get respite from the cold and enjoyed a tasting here as well! They fill up quickly on the weekends so be prepared!

These wineries came highly recommended as well:

— Bleinheim Vineyards – 31 Blenheim Farm Charlottesville, VA 22902

They currently only take reservations for outdoor seating (as of February 2021).

— Barboursville Winery – 17655 Winery Rd, Barboursville, VA 22923

Guided tours of the winery are provided and the house looks stunning. They also seem to hold a number of unique events that I’d like the chance to check out in the future.

Outdoor Winter Weekend in Charlottesville, VA Activities

When we travel with Banjo, we want to make sure he gets worn out before we start our plans for the day, so we liked having the chance to check out some of the parks in the area. A winter weekend in Charlottesville can look magical when it snows!

Shop my outfit: Cream Coat, LL Bean Boots, Leather Leggings, Tan Weekender Sweater

— Forest Hills Park 1022 Forest Hills Ave, Charlottesville, VA 22903// An impressive park with picnicking areas, a water park, sports courts, and even a forested path that is pretty magical in the snow.

— Kemper Park 503 Thomas Jefferson Pkwy, Charlottesville, VA 22902// This is Monticello’s 89-acre park but there is a 2-mile trail and it’s a beautifully kept park.

— Shenandoah National Park If you don’t mind driving, Shenandoah National Forest is located about 40 minutes outside of Charlottesville, VA. You do have to pay for park entry. You can buy your pass online here. Driving along the Blue Ridge is always a pleasure!

Monticello – although we did not visit Monticello on our trip this weekend, it is apparently a must-do. Especially if you love history, make sure to include this in your itinerary.

Carter’s Mountain – Carter’s Mountain is known to have the best views in Charlottesville, VA. The weekend we visited had a winter storm warning so it was closed.

Walk the Downtown Mall – The downtown mall is one of the longest pedestrian malls in the U.S. and runs for eight blocks. You could easily spend a few hours here doing some shopping.

Where to Eat

BREAKFAST

— Marie Bette’s – fresh-baked pastries (pain au chocolat!), coffee, and breakfast sandwiches. So yum.

— Bodo’s Bagels – they were closed on the day we went but this one came highly recommended.

— Farm Bell Kitchen – this restaurant was within walking distance of our hotel and we loved their brunch options! We got takeout but the interior of the restaurant is darling.

LUNCH

— We grabbed lunch at the wineries but Dr. Ho’s Pizza also came highly recommended 4916 Plank Rd, North Garden VA 22920

They were closed on the day we planned to get them! They are located close to Pippen Hill Farm & Vineyards so I would check them out for lunch if you do happen to be near Pippen.

DINNER

— Petit Pois – I adore french restaurants and this one is intimate. There is plenty of outdoor seating offered as well as limited indoor seating.

— Lampo – this one came highly recommended for some pizza.

— DOMA Korean Kitchen – I was craving Korean food after a day of exploring wineries and this one hit the spot for some takeout. This restaurant was also within walking distance of our hotel which was a plus!

— *The Inn at Little Washington* – now this one is a drive (an hour and 15 minutes from Charlottesville, VA) but we had our Valentine’s Day Dinner. It is a three-star Michelin restaurant which means it is “worth the journey ;)” If you’d like to read about our experience, check it out here.

— Michie Tavern – 683 Thomas Jefferson Pkwy, Charlottesville, VA 22902

This spot popped up when I was doing my research as a historical tavern that serves Southern fare. If you are planning a day with Monticello, I think eating here would be fun!

COFFEE / DESSERT

— Mudhouse Coffee Roasters– they are located in the Downtown Mall so if you need a cup of coffee while exploring, this is a great spot to stop by!

— Kung Fu Tea – Okay, you already know I was MORE THAN ecstatic to see a Kung Fu tea was within walking distance from our hotel. We definitely took advantage and treated ourselves to some bubble tea.

— Gearhart’s Fine Chocolates – this place came highly recommended for artisan chocolate. We didn’t personally make it there but I did see Gearhart’s chocolates offered at the wineries we visited as well! They have won awards for their chocolate and been featured multiple times so they will definitely be worth a visit.

What To Pack

A winter visit to Charlottesville, VA from January to February will probably bring snow (and even ice!) The weather was in the low 30s to high 40s consistently through the weekend. I would make sure to add these to your packing list for a romantic winter weekend in Charlottesville, VA!

1. Snow Boots – I love my LL Bean Boots
2. Outer Layers (A warm winter coat, gloves, hat, scarf) – My Patagonia jacket and North Face gloves kept me very warm.
3. Waterproof Layer – this rain jacket is sleek!
4. An umbrella (in case it rains/sleets!)
5. Sweater – I love my tan weekender sweater for traveling
6. Date Night Dress
7. Booties
8. Wide Brim Hat – this hat came in handy especially for shielding the sleet

Sample Itinerary

All in all, we had a perfect Valentine’s Day weekend. I would very much like to visit again in the Spring or the Fall!

Shop my outfits: Moss Green Jumpsuit, Fuscia Red/Pink Dress, Black heels

Would you go to Charlottesville, VA?