9 Historical Things to Do in Charlottesville - Trip Canvas
Editor Pick
9 Historical Things to Do in Charlottesville
Published: April 07, 2023
Written byAAA Travel Editor, Sherry Mims
Traveling through Central Virginia, you’ll notice not only bucolic scenery but also reminders of Americans who left a mark on our nation. Two presidents called the city home (Thomas Jefferson and James Monroe), while a third (James Madison) lived nearby. However, the region’s history is also deeply intertwined with the contributions of enslaved laborers, whose work shaped many of the landmarks we see today, including the University of Virginia. With comprehensive historical exhibits, monuments and tours, and some of the best restaurants in Charlottesville to visit, you too can make the most of your time in this historic region.
AAA / Sherry Mims
Charlottesville Downtown Pedestrian Mall
E. Main St.
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 December, 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.
AAA / Sherry Mims
The Inn at Monticello
1188 Scottsville Rd (Rt 20)
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.
iStockphoto.com / foodandwinephotography
The Ivy Inn Restaurant
2244 Old Ivy Rd.
Savor seasonal foods and fine wines in a circa 1816 establishment, encompassing four dining rooms and a garden patio. Once a tollhouse, the kitchen area at The Ivy Inn Restaurant 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.
Wikimedia Commons / Pthomaskmadigan
James Madison’s Montpelier
11350 Constitution Hwy.
Take time for a day trip from 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.
AAA / Sherry Mims
James Monroe's Highland
2050 James Monroe Pkwy.
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.
flickr / CC BY
Jefferson Vineyards
1353 Thomas Jefferson Pkwy.
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), a stop at Jefferson Vineyards adds a splash of fun to any itinerary based on Charlottesville history.
Wikimedia Commons / Billy Hathorn
Michie Tavern ca 1784
683 Thomas Jefferson Pkwy.
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 of Michie Tavern for a buffet with home-style favorites such as fried chicken, black-eyed peas and cornbread. If you have, room try the peach cobbler, an 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.
AAA / Michael L. Camarano
Monticello
931 Thomas Jefferson Pkwy.
Thomas Jefferson, the third president of the United States, designed and continually refined his neoclassical villa-style Monticello, a must-see for most visitors to Charlottesville. Located just over an hour from Richmond and about two-and-a-half hours from Washington, D.C., this historic presidential home in Virginia offers an educational experience well worth the journey. Once in 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 leader who authored the Declaration of Independence and yet owned a plantation with enslaved laborers. 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.
photohoo / iStockphoto.com
University of Virginia
1826 University Ave.
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. East of the rotunda is the Memorial to Enslaved Laborers, which honors the 4,000 enslaved people who lived and labored there between 1817 and 1865.
Sherry is an experienced #AAAEditor and former journalist who enjoys writing informative travel articles and reviews. Her commitment to making meaningful connections with people and places fuels her work for AAA. Favorite activities range from skiing to backpacking abroad and taking ghost tours.
THE VALUE OF TRIP CANVAS
Travel Like an Expert with AAA and Trip Canvas
Get Ideas from the Pros
As one of the largest travel agencies in North America, we have a wealth of recommendations to share! Browse our articles and videos for inspiration, or dive right in with preplanned AAA Road Trips, cruises and vacation tours.
Build and Research Your Options
Save and organize every aspect of your trip including cruises, hotels, activities, transportation and more. Book hotels confidently using our AAA Diamond Designations and verified reviews.
Book Everything in One Place
From cruises to day tours, buy all parts of your vacation in one transaction, or work with our nationwide network of AAA Travel Agents to secure the trip of your dreams!