History, Art and Wine in Charlottesville, Virginia


For a small university town, Charlottesville, Virginia has a lot going on. Nestled in the rolling hills at the base of the Blue Ridge Mountains, Charlottesville is steeped in early-American history, enjoys a rich arts and entertainment scene, and is surrounded by orchards and vineyards.

Charlottesville History


Thomas Jefferson’s Rotunda at the University of Virginia. Photo: Wikipedia

Charlottesville is nearly synonymous with Thomas Jefferson, the third President of the United States. His creative architecture is showcased in his lasting academic legacy, the University of Virginia (UVA). Jefferson designed what he call an “Academical Village” consisting of two rows of Pavilions, connected by colonnaded walkways flanking the rectangular Lawn. At the head of the Lawn, the Pantheon-inspired Rotunda is the signature landmark of the university. UVA has been designated a UNESCO World Heritage site as “a unique artistic achievement, a masterpiece of creative genius … associated with ideas, beliefs, and events of outstanding universal significance.” Free guided tours of the Rotunda are offered multiple times daily. Jefferson’s home,


Thomas Jefferson’s home, Monticello. Photo: Virginia Tourism Corporation

Monticello, is also designated a UNESCO World Heritage site. The neoclassical design embodies Jefferson’s ideas of the importance of public and private life. He installed ingenious little inventions throughout the estate, such as semi-automatic glass doors and a built-in bed he could enter from his study or bedroom. Mulberry Row is a collection of plantation buildings including former slave quarters, storehouses, a smokehouse and a dairy that operated as a small city within the estate. Guided tours are offered daily.


James Monroe’s home Ashlawn Highland. Photo: Wikipedia

Ashlawn Highland is the expansive plantation home of James Monroe, the fifth President of the United States and good friend of Thomas Jefferson. The 550-acres estate is exhibited as a working farm, with demonstrations of spinning, weaving and open hearth cooking. Highlights include tours of the refurbished home, lovely herb and vegetable gardens and 200 year old boxwood gardens.

Charlottesville Arts and Entertainment


Charlottesville Downtown Mall is a pedestrian-friendly hub of activity. Photo: Wikipedia

Arts and entertainment opportunities in Charlottesville are truly surprising for a city of less than 50,000 residents. It consistently draws big name entertainers like Lady Gaga, Taylor Swift and Bruce Springsteen and is an incubator for emerging artists – Dave Matthews got his start there.

Charlottesville also loves a good festival and you can find some sort of event almost every week. Some notable ones include the Virginia Festival of the Book (March), Historic Garden Week (April), the Virginia Film Festival (October) and a premier steeplechase called the Foxfield Races (April and September). Smaller events honor local harvests with celebrations of apple butter, salsa and wine.

For the visual art aficionado, there are dozens of art galleries and museums to browse. The brick downtown pedestrian mall is lined with galleries, bookstores, musicians and trendy restaurants. Speaking of restaurants, Charlottesville boasts over 100 entrepreneurial food venues ranging from formal dining to street food, that create mouthwatering menus using the freshest local produce and meats.

Vineyards, Breweries and Orchards


Wine Love at the Veritas Vineyard & Winery tasting room. Photo: veritas.com

Thomas Jefferson bestowed another legacy on Virginia: he was the first Virginian to plant acres of grape vines and attempt wine-making on a large scale. He wasn’t very successful, but two hundred years later, the vineyards throughout the Monticello American Viticultural Area have come into their own and produce some of the best wines in the Eastern U.S. More than 20 vineyards along the Monticello Wine Trail offer tours, tastings and special events in beautiful settings.

For those that prefer craft beers, the Brew Ridge Trail prides itself on having “more breweries than stoplights.” Six small-batch breweries offer tastings of their award-winning hops creations. The perfect agricultural conditions of the region also support dozens of orchards where residents and visitors alike flock to pick their own strawberries, peaches, apples and pumpkins. You can also taste and purchase ciders, preserves and other farm-fresh delicacies.

Covington Travel in Charlottesville

Covington Travel operates a Charlottesville branch at 1404 Greenbrier Place. Whether you are a local resident traveling away from home or visiting Virginia from afar, our Charlottesville team is ready to assist you with all of your vacation and business travel needs. And if you just want a recommendation for a restaurant or winery visit, they are happy to share their insider knowledge of this charming little city.


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