9 Historical Things to Do in Charlottesville

The brick-lined streets where presidents once strolled remains the place to go for local restaurants, shops and entertainment venues—ranging from lounges and historic theaters to a 3,500-seat amphitheater. Several Charlottesville hotels also are located within the city center, allowing for convenient access to University of Virginia and local events, notably First Fridays Art Walks at local galleries and the Charlottesville City Market, each Saturday April through Dec., at 100 Water Street. Other things to see in the city center include the Downtown Visitors Center (610 E. Main St.), Fourth Street (also known as Heather Heyer Way), and the Virginia Discovery Museum, an interactive children’s museum at 524 E. Main St.

Perusing Charlottesville hotels? Consider a 19th century bed-and-breakfast instead. Nestled in the hills around Monticello, this inn offers rooms named after the first five presidents and features locally inspired artwork. Walk the nearby trails or simply relax with a book in the common areas or on the grounds. If you reserve the cottage, take time to inquire about the antique bed’s canopy, which holds special significance to the family who owns the inn.

Savor seasonal foods and fine wines in a circa 1816 establishment, which encompasses four dining rooms and garden patio. Once a tollhouse, the kitchen area once again welcomes travelers and locals alike. Later, the property belonged to the larger Faulkner House estate, which was named after renowned novelist William Faulkner, a University of Virginia writer-in-residence. Since 1995, Chef Angelo Vangelopoulos and his family have owned and operated the fine-dining restaurant.

Take time for a day trip from the city of Charlottesville to see the home of James Madison, the nation’s fourth president, who led the nation during the War of 1812. James and Dolley Madison returned after his retirement to Montpelier. The Madisons extensively changed the structure—built circa 1760 by his father—as did later owners, including Marion duPont, a horse-racing enthusiast who willed the estate to the National Trust. A number of tours are available, with subject matter such as Madison’s constitutional work, Dolley’s role and the enslaved community’s experience, which provides an additional perspective of life at Montpelier.

A beautiful tree-lined drive leads visitors to James Monroe’s Highland, once called Ash Lawn-Highland, built close to Thomas Jefferson’s Monticello at Jefferson’s suggestion. Thought once to be a rather modest residence for the time, the presumed home—thanks to a 2016 excavation—proved to be a later addition to the property of the fifth president. Like Jefferson, he expressed opposition to the institution of slavery, yet used enslaved labor on his plantation. Though the home itself is from a later period, authentic furniture and other family pieces effectively portray the life and times of the Monroes.

With 193 acres of his land, Thomas Jefferson had hoped Italian immigrant Filippo Mazzei would cultivate grapes, olives and other crops that would thrive in Virginia. Although the original experiment failed, viticulture eventually returned to the property in Charlottesville. With a tour and award-winning wines, such as the 2013 Viognier (featuring the state grape of Virginia), this stop adds a splash of fun to any itinerary based on Charlottesville history.

Step back into Colonial times as costumed interpreters showcase what daily life was like in early America. The tavern, originally on a stage coach route, offered food and board up until the Civil War. Walk over to the restaurant portion for a buffet with home-style favorites such as fried chicken, black-eyed peas and cornbread. If you have room try the peach cobbler, then walk it off as you visit the rustic outbuildings, including a tavern gift shop, armory and artifacts shop, metal smith shop, and mill and general store.

Thomas Jefferson, the third president of the United States, designed and constantly updated his neoclassical villa-style Monticello, a must-see for most visitors to Charlottesville. Start your visit at the David M. Rubenstein Visitor Center and Carl and Hunter Smith Education Center, where you can watch an orientation film and learn more about Jefferson, a complex leader who authored the Declaration of Independence and yet owned a plantation with slaves. A variety of specialized tours are offered of the home and gardens, including one that presents daily life through the perspective of the enslaved Hemings family.

Named the Academical Village by Thomas Jefferson, these original buildings designed by the former president remain the centerpiece of the University of Virginia as well as a UNESCO World Heritage Site, and visitors are welcome to stroll independently or take a tour. The striking rotunda—modeled after the Pantheon in Rome—features Alexander Galt’s famous statue of Jefferson, classrooms and space to study and socialize.

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