Things To Do
Thomas Jefferson's Monticello
Visit the home of Thomas Jefferson, one of our Founding Fathers. We recommend the Behind the Scenes tour.
James Madison's Montpelier
Come learn about the father of the Constitution (one of our favorite shared documents).
Downtown Mall
One of our favorite things to do is wander along the downtown mall checking out the many restaurants and shops. Some of our favorites to check out are: Hello Comics, Bittersweet Clothing and Accessories, and Rock Paper Scissors. Our welcome party will be on the Downtown Mall so we encourage you to check out the area before the party!
The Alley Light
We stop by Alley Light for a cocktail every time we are in Charlottesville. Pete spent many of his law school days and nights here!
Tavola
We love spending a cozy night at Tavola enjoying their Italian food.
Monsoon Siam
Our favorite Thai restaurant in Charlottesville. We love grabbing lunch here before walking around the downtown mall.
Belle
A great option for brunch or coffee with a cute outdoor space. in the Belmont area of Charlottesville. We love the donuts and the whole wheat sourdough bread, made in house. Fair warning - some of the pastries tend to sell out early on the weekend!
Dairy Market Charlottesville
The Dairy Market is a new(ish) casual food hall. We recommend this option for a group, since everyone can get what they want. We also like the nicer, sit-down Latin American grill, South and Central, which is located within The Dairy Market.
Oakhart Social
This is one of our favorite restaurants in Charlottesville and is a good option close to the downtown mall. We like their wood-fired pizza and the pork steaks.
Pippin Hill Farm & Vineyards
Charlottesville is known for its wineries with gorgeous views. It was actually ranked Wine Enthusiast's Wine Region of the Year in 2023. Pippin Hill is a Charlottesville favorite. We recommend making a reservation before visiting Pippin Hill because it may be difficult to get a table otherwise. We love the seasonal pizzas from the kitchen as well.
Keswick Vineyards
We came here on our first trip to Charlottesville together. We like this winery for the live music and casual vibes.
King Family Vineyards
We recommend visiting on Sunday to watch their live polo matches. Feel free to bring your own sandwiches and snacks.
Hazy Mountain Vineyards & Brewery
This newer vineyard has arguably the best views in all of Charlottesville, despite the fact that Irina thinks the building itself looks a little like an Olive Garden. We are unclear on whether they have unlimited soup, salad, and breadsticks.
The Saunders-Monticello Trail
The Monticello Loop is a nice, easy hike around Monticello. Stop at Michie Tavern afterwards for a traditional colonial meal.
Carter Mountain Orchard and Country Store
We recommend getting a cup of Carter Mountain's warm apple cider and pairing it with a hot apple cider donut. We typically bring two dozen of the donuts home with us - we like them that much! Please keep in mind that in the fall, if you plan on parking and walking around, you will need to get a timed entry ticket from their website.