From its early days as a colonial settlement to its role in the Civil War and beyond, Charlottesville’s story is a microcosm of the broader American experience. The city's history harkens back to the mid-18th century when European settlers began establishing the first homesteads throughout the region. Over time, a few of those enterprising pioneers started to conduct trade along a thoroughfare known as the “Three Notched Road,” and formed a small village in the process. The local leaders of the surrounding Albemarle County in turn decided to officially charter the community in 1762, calling it “Charlottesville” after the wife of the reigning British King George III, Queen Charlotte Sophia of Mecklenburg. Although the settlement remained small for many years after, it thrived as a regional economic center due to the continued trade along the Three Notched Road and the nearby Rivanna River. But its diminutive nature did not dissuade influential people from moving to the vicinity. One of the most significant figures in Charlottesville’s history is Thomas Jefferson, the third President of the United States and the principal author of the Declaration of Independence. In 1768, Jefferson began constructing a beautiful mansion atop a hill right outside of town. Called “Monticello”—or “little mountain”—Jefferson designed the structure based upon the neoclassical principles of the great Italian architect Andrea Palladio.  

Indeed, Jefferson’s blueprints incorporated some of the most recognizable elements of Palladian motifs, such as symmetry, classical forms, and harmonious proportions. But the house featured several distinctive architectural innovations, like an octagonal room, a revolving bookstand, and a dumbwaiter for wine. While Monticello was celebrated for its architectural beauty, it was a working plantation that relied on the labor of enslaved people. In fact. Jefferson owned over 600 slaves during his lifetime, and their contributions were integral to the estate’s operations. (Among the enslaved families living at Monticello were the Hemings, whose member, Sally, is believed to have had a long-term relationship with Jefferson.) Jefferson would spend the rest of his life at Monticello, pursuing an extensive variety of projects that fueled his passion for agriculture, architecture, and technology. His most notable endeavors involved the creation of the University of Virginia in Charlottesville during the early 19th century. Envisioning the campus to serve as an “academic village” Jefferson hoped the school would foster a greater community where students and professors could learn together. He worked alongside noted architect Thomas R. Blackburn to design its initial layout, going as far as to design some of the buildings including its famed Rotunda.  

Meanwhile, Charlottesville kept growing steadily, eventually reaching the scale of an actual city by the middle of the century. Its continued economic prosperity eventually made it a strategic asset during the American Civil War, functioning as an important Confederate supply base for units stationed all over Virginia. After the war, Charlottesville, like much of the South, faced the challenges of Reconstruction and the long struggle for civil rights. This fight persisted into the 20th century, with Charlottesville emerging as a focal point for the wider Civil Rights Movement of the 1950s and 1960s. The legacy of this struggle is evident in the city’s ongoing efforts to address racial inequality and promote social justice.

Charlottesville today is celebrated for its rich diversity, vibrant arts scene, and fascinating cultural institutions. Cultural heritage travelers have especially enjoyed visiting renowned landmarks like the Historic Downtown Mall, Jefferson Theater, IX Art Park, President James Madison’s Highland, and the Jefferson School African American Heritage Center. Two of its most famous historic sites—the University of Virginia and Thomas Jefferson’s Monticello—are designated UNESCO World Heritage Sites. From its colonial roots to its modern-day struggles and triumphs, the city embodies the spirit of America—a place where history is ever-present, and the future is continually being shaped. 

Keswick Hall stands as one of the best surviving examples of Italianate-style architecture in Virginia today. One of the first examples of Renaissance Revival-style architecture, Italianate design principles themselves are some of the most historic ever used in the United States. Despite its popularity in the United States, it was originally conceived by a British architect named John Nash at the beginning of the 1800s. Inspired by the architectural motifs of 16th-century Italy, he constructed a brilliant Mediterranean-themed estate called “Cronkhill” in his native England. Nash had borrowed heavily from both Palladianism and Neoclassicism to design the building, both of which were derivatives of the Italian Renaissance art forms. Soon enough, many other architects began copying Nash’s style, using it to construct similar manors across the English countryside. However, the person responsible for popularizing the aesthetic the most was Sir Charles Barry, who had his own offshoot called “Barryesque.” By the middle of the century, this Italian Renaissance Revival-style architecture had spread to other places within the British Empire, as well as mainland Europe. It had crossed the Atlantic during the 1830s, where it dominated the American architectural landscape for the next 50 years. Architect Alexander Jackson Davis promoted the style, using it to design such iconic structures as Blandwood and Winyah Park in New York. Although he was more widely known for his use of another Revival style—Neo Gothic—his work with Italianate helped cement it within the United States. 

Margaret Thatcher, Prime Minister of the United Kingdom (1979 – 1990) 

Hillary Clinton, 67th U.S. Secretary of States (2009 – 2013), U.S. Senator from New York (2001 – 2009), and former First Lady of the United States (1993 – 2001) 

Bill Clinton, 42nd President of the United States (1993 – 2001)  

The Four Seasons (1981)