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People from various generations will enjoy 2 days in Charlottesville. This central Virginia city, boasting a rich history dating back to the Founding Fathers, has appealed to older visitors for many years. As the demographic of visitors changes to younger generations, the focus shifts to interests dear to Millennial and Gen X hearts: wineries, cutting-edge art, and outdoor adventure. C'ville, as it is popularly known, percolates with the youthful energy of a university town, and its proximity to the Blue Ridge Mountains offers plenty of opportunities to blow off steam.
Monticello, home of Thomas Jefferson in Charlottesville, Virginia, is a UNESCO World Heritage site. Photo by Katherine Rodeghier
Charlottesville and surrounding Albemarle County have a complicated past. Civic leaders are working with community members and descendants to ensure its stories are historically accurate and inclusive while openly addressing the complex nature of slavery.
A costumed interpreter portrays Thomas Jefferson during tours of Monticello. Photo by Katherine Rodeghier
These efforts are evident at Jefferson's Monticello, a UNESCO World Heritage site. The author of the Declaration of Independence, and the third U.S. president, enslaved more than 600 people during his lifetime, with about 400 living at Monticello. Twenty years ago, a tour of Jefferson's plantation barely mentioned them. Today, their story has become a significant part of the visitor experience through exhibits, films, and guided tours.
Tours depict slavery on the plantation Thomas Jefferson owned in Charlottesville, Virginia. Photo by Katherine Rodeghier
The “From Slavery to Freedom Tour” is one example. It explores the plantation from the perspective of its enslaved people. The entire exhibit space is devoted to the story of Sally Hemings, an enslaved woman of European and African descent thought to be the concubine of the widowed Jefferson. A display board giving her brief biography states: “Mother of at least six children fathered by Jefferson between 1790 and 1808.”
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The fourth and fifth U.S. presidents also had estates in the Charlottesville area. James Monroe's Highland and James Madison's Montpelier are open for tours and include stories of enslaved people who toiled there.
Jefferson founded and designed the University of Virginia, a UNESCO World Heritage site in Charlottesville. Guided historical and architectural tours feature the Rotunda, modeled after the Pantheon in Rome, and Jefferson's Academical Village with its pavilions and student rooms, including one once occupied by Edgar Allan Poe. But visitors do not need to join a tour to stroll the grounds, take selfies on The Lawn and peek behind the serpentine walls Jefferson designed to enclose gardens.
The student room once occupied by Edgar Allan Poe is part of a tour of the University of Virginia grounds. Photo by Katherine Rodeghier
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Enslaved people built and worked at the university for more than four decades, a fact acknowledged at the Memorial to Enslaved Laborers.
The Memorial to Enslaved Laborers tells the story of enslaved people who built and maintained the University of Virginia. Photo by Katherine Rodeghier
The Memorial to Enslaved Laborers began as a student-led effort in 2010, and in 2020 it was unveiled to the public. Two engraved granite rings honor more than 4,000 enslaved people who were fundamental to everyday life and the economic success of the university. One inscription reads: “1825-29 Thrimston Hern, ‘a tolerable good stone cutter,' does stone work at UVA, including completing the Rotunda steps.” Other inscriptions are chilling: “1856 An enslaved eleven-year-old girl is beaten unconscious by a UVA student. Claiming his right to discipline any slave, he suffers no consequences.”
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An old textile factory has become a place to play and innovatively enjoy art. The IX Art Park is a kaleidoscope of outdoor murals and sculptures delighting kids and adults alike. Some evenings, festivals, musical acts, and films occupy an outdoor stage, and a farmers market fills the park on Saturday mornings during the growing season. Inside an old warehouse, The Looking Glass immersive art experience doubled in size in 2021, expanding to 6,000 square feet of light, sound, color, and hands-on installations.
An old textile factory has been converted to IX Art Park. Photo by Katherine Rodeghier
Free, live concerts draw crowds to the Ting Pavilion for Fridays After Five. From spring through early fall, festivalgoers pick up food and libations from vendors on Friday nights and settle in on the lawn or under the pavilion to enjoy performances by local artists.
Free concerts are staged at the Ting Pavilion in downtown Charlottesville. Photo by Katherine Rodeghier
The pavilion occupies the east end of C’ville’s downtown mall, an eight-block, brick-paved pedestrian section of Main Street. Four bookstores are among the 120 shops and 30 restaurants housed in renovated historic buildings. The Paramount Theater, a restored 1930s movie palace, stages various arts performances.
Charlottesville’s Downtown Mall is a pedestrian-only section of Main Street. Photo by Katherine Rodeghier
Charlottesville sits in the heart of Virginia’s wine country. The Monticello Wine Trail, inspired by the enology dabblings of Thomas Jefferson, comprises 40 wineries within 25 miles of C’ville. A digital passport allows visitors to check into wineries along the trail and receive a complimentary wine glass after their 10th visit. You can arrange a guided private wine tour or set out and explore on your own.
Barboursville Vineyards is one of 40 wineries on the Monticello Wine Trail. Photo by Katherine Rodeghier
Pippin Hill Farm & Vineyards, a seasonal agritourism spot, has kitchen gardens, cooking classes, farm-to-table wine pairings, winery tours, and tastings. Barboursville Vineyards, on the former estate of Governor and U.S. Senator James Barbour, is renowned for growing European-style, estate-bottled wines. In addition to tours and tastings, it serves lunch and dinner in its Palladio Restaurant and offers overnight accommodations in its 1804 Inn and Vineyard Cottages.
Guests enjoy farm-to-table wine pairings at Pippin Hill Farm & Vineyards. Photo by Katherine Rodeghier
The boutique Glass House Winery takes its name from its tropical conservatory. Along with producing wine, it makes handcrafted chocolates, has live music events on Sundays in the open season, and operates a bed-and-breakfast.
Sunday visitors gather on the lawn at Glass House Winery, named for its tropical plant conservatory. Photo by Katherine Rodeghier
Not to be outdone by wine, the C'ville area also has more than 20 craft breweries, cideries, and distilleries. Three Notch'd Brewing Company next to IX Art Park takes its name from Three Notch'd Road, a Native American footpath nearby. C'ville grew on the trail's east-west axis, blazed by three markings on trees along its path. It became a major colonial road west of the James River in Richmond, Virginia, to the Blue Ridge Mountains. The brewery's Minute Man beer, named in a nod to C'ville's Revolutionary War heritage, has been ranked the No. 10 IPA in America by Draft Magazine.
Editor's Note: For a fun day-trip excursion, if you have one extra day, we recommend checking out nearby Albemarle CideWorks. This is a short drive from central C'ville and makes for a pleasant outing.
There are several different hard apple ciders available from Albemarle CiderWorks. Photo courtesy Albemarle CiderWorks
The Blue Ridge Mountains, a segment of the Appalachians, is the defining geographic feature in and around C'ville. Trails range from easy to rugged, including a long section of the Appalachian Trail. Hikers flock to Shenandoah National Park, a long, skinny slice of the Blue Ridge 20 miles west of the city.
Hikers follow the Appalachian Trail through Shenandoah National Park west of Charlottesville. Photo by Katherine Rodeghier
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Skyline Drive runs along the park's spine from Milepost 0 at Front Royal, Virginia, south to Milepost 105 at Rockfish Gap and ranks among America’s top scenic drives.
Road-trippers take scenic drives along the Blue Ridge Parkway and Skyline Drive in Shenandoah National Park. Photo by Katherine Rodeghier
The Blue Ridge Parkway meanders 469 miles south of Shenandoah National Park to Great Smoky Mountains National Park. Begun as a work project during the Depression, it's one of the most famous road trips in the U.S. Hiking trails spiral off the two-lane road. One of the closest to Charlottesville, the rugged Humpback Rocks Trail, is named for the rock formation wagon trails used to guide them over the mountains in the 1840s.
The Blue Ridge Mountains offer many options for outdoor recreation in Charlottesville. Photo by Katherine Rodeghier
Water enthusiasts in Charlottesville go to the Rivanna River for guided or self-guided trips from the spring to the fall. It is a designated scenic river running 46 miles from C'ville to its confluence with the James River. The Rivanna River Co has kayaks, canoes, tubes, and stand-up paddleboards, supplies life jackets, and arranges shuttle service.
Hot air ballooning provides an unusual perspective for viewing Charlottesville and the Blue Ridge Mountains. Monticello Country Ballooning and Blue Ridge Balloon offer flights skimming over the tree tops in the foothills of the mountains and floating over farms in Albemarle County.
Hot air balloons float above the foothills of the Blue Ridge Mountains outside Charlottesville. Photo by Katherine Rodeghier
For an aerial view of Charlottesville and the Blue Ridge Mountains from solid ground, motorists drive up to Carter Mountain Orchard, a five-generation family farm offering u-pick fruit, a country store, and a concession stand. Live music and food trucks add a festive atmosphere on some summer evenings. And the orchard's cider doughnuts are incredible.
Check the University of Virginia calendar before planning a trip to C'ville to avoid large university events such as homecoming, parent's weekend, home football games, and move-in and move-out periods. A university of nearly 22,000 students impacts a city of 47,000 (109,000 in Albemarle County), leading to crowds, traffic jams, and sold-out accommodations at peak times.
Time a visit to Charlottesville when there are no major events at the University of Virginia. Photo by Katherine Rodeghier
Spring and fall are the best times to plan 2 days in Charlottesville. Summer can be oppressively hot. Winters can be icy enough to make driving difficult and temperatures too low for some activities.
University of Virginia rotunda. Photo by Katherine Rodeghier
The city is 117 miles southwest of Washington, D.C., 72 miles northwest of Richmond, Virginia, and 250 miles east of Charleston, West Virginia. Charlottesville Albemarle Airport (CHO), eight miles from downtown C’ville, has flights to and from Charlotte, Philadelphia, New York/LaGuardia, Washington/Dulles, Atlanta, and Chicago. C’ville’s Amtrak station lies between downtown and the university. Amtrak has passenger service on its Cardinal, Crescent, and Northeast Regional lines to major cities, including Washington, Philadelphia, New York, Providence, Boston, Charlotte, Atlanta, Birmingham, New Orleans, and Chicago.
Editor's Note: If you want a charming stay while visiting Charlottesville, we recommend checking out The Clifton Inn. The food and the stay offer a luxurious stay, surrounded by the area's history.
Visitors feel welcome from the moment they drive up to the Clifton Inn. Photo courtesy Clifton Inn
Charlottesville Area Transit, the CAT, has buses six days a week, usually beginning or ending at the east end of the Downtown Mall. The Charlottesville Free Trolley operates six days a week between the university and Downtown Mall.
While Charlottesville has rideshares and taxis, renting a car at the airport would be the best option for 2 days in Charlottesville, particularly for drives to Shenandoah National Park and the Blue Ridge Parkway. There is more to see and do in Charlottesville, but if you only have two days, these are some of the things not to miss. Check out more recommendations on Wander with Wonder for what to do and see when you visit Virginia. We also have more 2 Days Ultimate Guides for those great short getaways.
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