This quaint and cute city is riddled with vineyards, museums, and boutique shops. It’s at the foot of the Blue Ridge Mountains too, so there are plenty of outdoor activities and stunning nature spots just round the corner!
You can’t skip the city’s UNESCO World Heritage Sites, Monticello and the Academical Village, and no holiday here would be complete without a trip to one of the 30 local vineyards.
The city offers a great balance of nature, culture, fun, and relaxation. Whether you decide to spend the day browsing the city’s museums, getting out into the wilderness, shopping in the Downtown, or visiting the homes of Jefferson and Monroe, you’ll be enchanted by all the things to do in Charlottesville.
James Monroe’s Highland
Wondering where the best history spots are in Charlottesville? Welcome to the old home of the fifth president of the United States, James Monroe’s Highland! This modest cottage property and its surrounding land were integral to the private life of the president.
Despite the beauty of the setting and the property itself, there is a darker history you’ll explore whilst you’re here – slavery. Between 1799 and 1865 Monroe owned 53 different slaves who worked the land and served the household against their will. In fact, of the 178 slaves Monroe had throughout his lifetime only one was ever set free.
As a political figure, Monroe presents contradictions, especially with regard to his views on slavery. He fought for the abolition of slavery, and simultaneously viewed the integration of Black Americans into society as a burden. Come and discover more at James Monroe’s Highland!
University of Virginia
The University of Virginia was founded back in 1819 by Thomas Jefferson. It was opened as a public university, which was a progressive choice at the time. It was ranked as the 4th Best Public National University in the US in 2022 by the U.S. News and World Report, and it attracts students from across the country to Charlottesville.
The University offers historical tours through the University Guide Service, which could be a great way to kill a morning or afternoon in Charlottesville if you’re a history enthusiast!
The campus is enchanting, with its stretches of well-kept lawn and Victorian-style buildings. It’s definitely worth taking an hour or two to explore the campus.
Historic Downtown Mall
The adorable brick-paved streets and red brick buildings that line the Historic Downtown Mall make for an enchanting shopping and dining experience. There are over 120 shops and 30 restaurants, so you won’t be short for choices!
Aside from that, there are a handful of performance venues in this area of the city, so if you want to watch a show or catch a movie it’s the perfect place to come.
The Historic Downtown Mall has been the epicenter of Charlottesville since 1974, and with its charming character and lively atmosphere it’s not hard to see why! It’s crazy to think that Monroe and Jefferson once strolled these very streets.
Monticello
Thomas Jefferson, who served as the third president of the United States between 1801 and 1809, cleared the top of the 868-foot Monticello Mountain and built his dream home, which he was always continuously remodeling, at the top. The house is a gorgeous Neoclassical mansion, surrounded by vast meadows and stretches of forest.
Monticello was originally a plantation, and there were up to 80 slaves working there at once, most under the age of sixteen. Jefferson sold and bought slaves, and it’s estimated he would of had about 200 slaves per year, distributed across Monticello and his other properties, Albermarle County farms and Poplar Forest estate.
The construction of the Monticello house began in 1769 and wasn’t complete until 1784. He later remodeled and enlarged the house between 1796 and 1809. There are a total of 43 rooms across the property! Come and admire the grandeur and intricate decor of the property, and find out more about Monticello’s history and inhabitants.
Paramount Theater
Wondering where the best entertainment spots are in Charlottesville? Well, this one is famed as the best in the city. The Paramount Theater is backed by a long history, too. It opened up in 1931 with a screening of Touchdown.
It’s lived through a lot, from desegregating in 1964 when the Civil Rights Act was finally passed, to surviving the COVID pandemic most recently. It shut down in 1974 for almost 20 years, but was revived once again by the community.
The Paramount Theater is mostly run by eager volunteers who see it as an important hub for the local community and a historical relic. From your favorite National Geographic documentaries to high end fashion shows and lively music concerts, there’s always something new on show at the Paramount Theater.
Blenheim Vineyards
The Blenheim Vineyards boast a stunning setting, with rolling hills and mountains stretching into the distance. It’s the perfect place to come and enjoy a warm afternoon sipping wine outside and catching up with a friend under the sun.
Their tasting room, a gorgeous wood and glass structure, has an enchanting rustic countryside feel and makes the most of the incredible surrounding vistas with large glass windows.
Sample their finest concoctions by the glass (or by the bottle!), from sweet and fruity roses to refreshing whites. It’s just 20 minutes away from Charlottesville, so the only thing that really needs to be decided is who will be the designated driver!
Skyline Drive in Shenandoah National Park
This stunning drive runs along the top of the Blue Ridge Mountains that sit in Shenandoah National Park. It’s some 105 miles long and it takes around three hours to drive the full length of the Skyline Drive. There’s a small fee to drive along this public road, but it’s worth it.
There are four different access points to the road, the Front Royal Entrance Station, Thornton Gap Entrance Station, Swift Run Gap Entrance Station, and the Rockfish Gap Entrance Station. GPS systems aren’t always the most reliable in this neck of the woods, so make sure you have a map downloaded or reliable directions!
The views along the way are absolutely stunning, especially in autumn when the mountains are littered with golden leaves and the sunset lights the sky with a bright orange hue. Keep a lookout for wildlife too, there’s black bears and coyotes nearby!
Carter Mountain Orchard
The Carter Mountain Orchard sits at the top of a hill with views of lush green valleys below. There is a cute red barn at the top and the orchard is just round the corner from Charlottesville.
Come and pick the peaches and apples they grow there, try their apple cider donuts (and apple cider!), and enjoy the fresh air and some time in the sun.
There are food trucks at the orchard on the weekend and they always have lots of different events on, with something for outdoor lovers of all ages!