Charlottesville, a medium sized city tucked in central Virginia in the shadow of the Blue Ridge Mountains, is the perfect place for a weekend getaway. This beautiful Southern city has something for everyone – great shopping and food, dozens of nearby wineries, museums, numerous places of interest for history buffs, beautiful architecture, and easy access to spectacular scenery and outdoor adventure.
Charlottesville was founded in 1762 along a trade route to Richmond. The fact that it was largely spared during the Civil War has contributed to its beauty. The Charlottesville area was home to three presidents, including Thomas Jefferson, James Monroe, and James Madison.
It should be noted that Charlottesville has a negative past related to racial division. The local African American population suffered greatly under Jim Crow laws, and segregation, lynchings and cross burnings have a history in the area. More recently, in 2017, the city was the site of violent racial riots. But the city is striving to heal and move forward, with Confederate named parks and streets being re-christened, and statues being replaced. The city has budgeted funding toward racial equity and inclusion, and the University of Virginia, with its student population, helps to provide a social balance.
I’ve visited Charlottesville numerous times, and have provided a guide of some of my favorite places to visit. Viator is a good site to purchase activities, such as wine and food tours in the Charlottesville area.
Charlottesville Attractions
Downtown Pedestrian Mall – The center of activity in downtown Charlottesville is along the seven block long pedestrian mall, built in 1974. Here, visitors can choose from a multitude of shops, boutiques, galleries, restaurants and other entertainment venues along an attractive, landscaped, brick paved pedestrian area. Many of the restaurants offer outdoor dining on the mall, perfect for people watching. On Saturday mornings (May through November), the Charlottesville City Market is held on the mall, and a Holiday Market is held in November / December.
University of Virginia – Founded by Thomas Jefferson in 1819, the highly ranked University of Virginia was the learning institution for notable alumni including Edgar Allan Poe, Georgia O’Keefe, Woodrow Wilson and Robert Kennedy. The campus is considered one of the most beautiful in America, with its Jeffersonian architecture. It is one of the few colleges listed as a UNESCO World Heritage Site.
Without a doubt, the most beautiful part of the campus is the Lawn, a large terraced grassy rectangular court surrounded by white colonnaded Neoclassical buildings designed by Jefferson. The Lawn was the original grounds of the university. At the north end of the Lawn sits the Rotunda, modeled after the much larger Roman Pantheon. It was used as a library, designed to represent the “authority of nature and power of reason”. Many consider the Rotunda’s center as a symbol of the separation of church and education, especially since most universities in the English-speaking world at the time had a church as their focus. On one memorable beautiful fall day, I relaxed on the Lawn surrounded by the colorful foliage of the ash and maple trees, watching students enjoying the day, reminiscing about my own college days.
The campus is located on the west side of Charlottesville off University Avenue. Along University Avenue are a number of shops, bars and restaurants, including the Virginian, a local institution since 1923. A free trolley operates every 15 minutes seven days a week between the downtown area and University of Virginia.
Fralin Museum of Art – Situated on the University of Virginia Campus, the Fralin Museum of Art has 14,000 objects ranging including American, European, Asian, African, Native American and Pre-Columbian art.
Monticello – Just south of Charlottesville, located off Thomas Jefferson Parkway, sits the stunning estate of Thomas Jefferson, the third President o f the United States, and author of the Declaration of Independence. My first visit to the estate was when I was seven years old, when my parents took us on an ‘educational vacation’ to Monticello, as well as nearby Williamsburg. I’ve visited numerous times since then. The estate spans 5,000 acres, and the original plantation was used to grow tobacco and other crops. The unique Neo-classical home was designed by Jefferson, and sits atop a hill with spectacular views. It’s centerpiece is the octagonal dome. The interior of the home houses a number of Jefferson’s inventions including the Great Clock, a copying machine, and revolving bookstand. It is the only private home in America to be designated as a UNESCO World Heritage Site. The restoration of the home and grounds, and museum programs provide an account of the lives of both the saves and free families. Monticello has burial grounds of Jefferson himself, his relatives, along with enslaved people.
Another way to get to Monticello is by hiking the Saunders-Monticello trail, a scenic four mile trail that starts in Kemper Park in Charlottesville, and offers views of the Blue Ridge Mountains.
Nearby Attractions
Shenandoah National Park / Skyline Drive – Shenandoah National Park extends along the Blue Ridge Mountains and is filled with forests, meadows, numerous waterfalls, and rocky peaks, including Old Rag, a favorite hiking spot. The park has a large network of trails, and is home to many bird species, plus deer, squirrels and the black bear. It also has several lodges and two visitor centers.
The 105 mile long Skyline Drive runs the length of the park, with numerous lookouts offering panoramic vistas of the Shenandoah Valley. The drive is especially beautiful during spring when wildflowers are prevalent, and fall when the foliage is stunning.
Montpelier – Located five miles northeast of Charlottesville in Orange, Virginia, is President James Madison’s Montpelier. The estate was the plantation of the Madison family, including the fourth president of the United States, James Madison, also known as the Father of the Constitution, and his wife, Dolly. The plantation was established by James Madison’s grandfather in 1723, and originally called Mount Pleasant. His son, James Madison Senior built the present home in 1764, with a number of extensions added later by James Madison Junior. The estate was later owned by the du Pont family, and sold to the National Trust for Historic Preservation in 1984. Today, visitors can tour the Georgian style home, learn the history of the Madison family, and learn about the slave labor that was used on the plantation. Visitors can also walk the beautiful grounds which offer views of the Blue Ridge Mountains. The grounds include formal gardens, the gravesite of President James Madison, and eight miles of walking trails. A number of events are held annually at Montpelier, including the Montpelier Hunt Races, the Montpelier Wine Festival, and the Fall Fiber Festival.
James Monroe’s Highland – Highland was the home and working plantation of America’s fifth president, James Monroe. He purchased the land in 1793, and moved to the property in 1799. Monroe was forced to sell the property in 1825 due to debts owed. The 535 acre estate and home is owned by the College of William and Mary, Monroe’s alma mater. On display is a Victorian style farmhouse, a reconstructed slave quarter, an overseer’s cabin, and an ice house.
Wineries and Cideries
Wine enthusiasts will love the Charlottesville region, with more than 40 wineries to choose from along the Monticello Wine Trail. Wine production in Virginia dates back to 1609, when settlers of Jamestown planted vines to produce a cash crop. Later, Thomas Jefferson had the vision for producing wine on his Monticello estate that would rival those of Europe. These early attempts failed due to disease, pests and weather. In the early 1800’s, the Norton grape was first cultivated in Virginia, and a Norton red wine produced by the Monticello Wine Company received an international award at the Vienna World’s Fair in 1873. Over the years, wine production in Virginia was still slow and difficult, with a lapse during prohibition. It wasn’t until the 1970’s that wine production really took off, and has continued to grow since then, with more than 300 wineries in the state today. In addition to wineries, the region is also home to numerous orchards and cideries worth visiting.
Barboursville Vineyards – One of my favorite wineries is Barboursville, the oldest, and one of the most beautiful vineyards in the region. Barboursville vineyards covers 180 acres and includes the remnants of an 18th Century estate for the Barbour family designed by Thomas Jefferson. The winery includes a restaurant, an inn and cottages available for rent.
Bold Rock – Near Monticello, the Bold Rock cidery offers visitors a taste of their award winning craft cider. The beautiful setting provides ample opportunities for enjoying views of the Blue Ridge Mountains.
Carter Mountain Orchard – With a beautiful setting, the Carter Mountain orchard is the perfect place to pick apples, strawberries, and peaches (between April and November). On Thursday evenings, visitors can enjoy dinner and hard cider or wine at picnic tables while watching the sunset. Musical entertainment and hayrides are offered, as well as special events such as the Apple Harvest Celebration, the Peach Festival, and an Easter Egg Hunt. An onsite country store sells fruit, vegetables, ciders, and desserts such as peach cider donuts and apple pie.
Restaurants
Ivy Inn – Housed in an 18th century home, the Ivy Inn is the perfect place for an elegant dinner. The interior has four dining rooms furnished with ceiling beams and a fireplace. The cuisine combines Southern favorites and international dishes.
Michie Tavern – Located just below Monticello, Michie Tavern is a historic pub built in 1784. The restaurant offers a lunch buffet of colonial comfort food such as fried chicken, hickory smoked pulled pork barbecue, ham, black-eyed peas, stewed tomatoes, cornbread and biscuits, served by waiters dressed in period costumes.
Citizen Burger Bar – Located on the downtown pedestrian mall, this popular establishment uses local farms as the source of its ingredients, including locally made buns, grassfed local beef and Virginia cheese.
Tavola – Located southeast of downtown on Monticello Road, Tavola specializes in Italian dishes, craft cocktails and cicchetti, small Venetian snacks.
Rapture – Located on the downtown pedestrian mall, with outdoor dining, Rapture’s menu includes steaks, pasta, seafood, burgers, and sandwiches. The outdoor dining area on the mall provides a nice spot to people watch.
Sultan Kebab – This Turkish restaurant is located on the south side of downtown, and has both indoor and outdoor dining areas. My favorites include the cheese filled phyllo pastry known as Borek, and the Iskender platter which includes a heaping mound of marinated sliced beef and lamb smothered in a tomato sauce and yoghurt, served with rice and salad.
The Virginian – Charlottesville’s oldest restaurant in operation since 1923, adjacent the University of Virginia. The menu includes salads, sandwiches, burgers, crab cakes, pastas, fried chicken and more.
Dairy Market food hall – Located west of downtown on Grady Avenue, this large hall contains multiple food vendors, including Filipino, Latin American, Italian, Southern, burgers, and more. The hall also has small boutiques, a bar, brewery, and holds numerous events.
Shenandoah Joe Coffee – This local coffee roaster has two locations in Charlottesville, offering 25 varieties of specialty and gourmet coffee.
Accommodations
Charlottesville has a wide array of accommodations, ranging from luxurious to budget, to meet the needs of every traveler. Lodging for any budget can be found on Booking.com or Trivago. On several occasions, we have stayed about thirty minutes north, at Lydia Mountain Lodge and cabins. Lydia Mountain is a great location for exploring the surrounding attractions, including wineries, Shenandoah National Park, Luray Caverns and Charlottesville. The lodge and cabins are secluded within a wooded area, and many of the cabins are pet friendly. Each cabin has a hot tub, perfect for soaking after a long day of excursions and hiking. A separate post includes more information about Lydia Mountain.
