A Historic Guide to Visiting Charlottesville, Virginia

A Historic Guide to Visiting Charlottesville, Virginia

City Guides

Andrea E. McHugh

Like many places in Virginia and beyond, Charlottesville’s name is rooted in English royalty (in this case, the namesake was Princess Charlotte, best known for marrying “mad King George”).  Today, the city is affectionately known to locals simply as “C’ville.” The Shenandoah Valley city is synonymous with Thomas Jefferson’s Monticello, the sprawling plantation designed by the third President of the United States who ultimately founded the University of Virginia there in 1819. But before being officially becoming a city in 1888, Charlottesville made its mark in the Revolutionary War housing British and German prisoners following the Battle of Saratoga. This is how downtown neighborhood “Barracks” got its name. Preceding the settlers, Native Americans including the Monasukapanough inhabited the area and blazed trails that became critical thoroughfares like Three Notch'd Road which set the blueprint for the main arteries that access Charlottesville from all points today.

Photo by Theresa White, Courtesy of Charlottesville Albemarle Convention & Visitors Bureau


As one may expect, there’s no shortage of lodging options in Charlottesville that boast Colonial styling and period detail. The Clifton, however, might be considered “peak C’ville” with its unique history. Originally built in 1799 for Thomas Jefferson’s eldest daughter Martha and her husband Thomas Mann Randolph, the 20-room inn is comprised of a collection of restored late 18th and early 19th century buildings throughout its 100-acre property. The Manor House, the one-time main home of the couple, shows reflections of its past via the six-pillared clapboard facade, countless pairs of wrought iron strap hinge shutters and original detail throughout. However, modern design, contemporary furniture and sophisticated artwork offer today’s visitor a distinctly luxe experience. Whether staying at The Manor House, The Carriage House, The Cottage, The Livery Stables or the nearby Collina, a five-room farmhouse, this secluded countryside compound will leave you wanting for nothing. (Insider’s Tip: A stay at The Clifton includes access to Common House Social Club in downtown Charlottesville.)

Another sprawling property steeped in history is Boar’s Head Resort, where a nineteenth century gristmill houses 39 of the resort's 170 guestrooms in addition to the Old Mill Room restaurant and Bistro 1834 (named in homage of the year the mill was founded). The mill survived burning orders orders from Generals Grant and Custer during their march through Charlottesville in the Civil War. After being relocated piece by piece from its original site on the Hardware River, the building became today’s resort, where original fieldstone, heart pine beams and planks, and massive grist stones are now prominently featured throughout. Boar's Head Resort was purchased in 1988 by the University of Virginia Foundation and is part of Historic Hotels of America.

If you prefer staying in the heart of it all, 200 South Street Inn may be your best bet. Built in 1856, this restored home was the first built on the block and over the past century and a half, has served as a private residence, a girls finishing school, a college student boarding house and most interestingly, a brothel (known legally in Virginia as a 'Bawdy House’). But today’s 200 South Street Inn, which includes a main house and neighboring cottage, is known for its Southern hospitality, generous rooms and meticulous detail. While the bulk of its original furnishings has been moved to the Valentine Museum in Richmond (just an hour’s drive away), you can learn about the antiques that do remain in a scrapbook onsite that catalogs each piece with its history.

Just outside your door is C’ville’s popular Downtown Mall, which gives pedestrians the opportunity to wander freely amongst the charming shops and eateries. You’re likely to encounter a busker or two to put a spring in your step, join an art walk, catch a flick in the historic movie theater or if it’s a Saturday (April through December), savor spoils from the local harvest at the farmer’s market (pro tip: don’t miss Albemarle Bakery’s just-out-of-the-oven baguettes).


History runs deep at the ca. 1784 Michie Tavern which has been serving up Southern fare for more than two centuries. Located a ½ mile below Jefferson’s Monticello, no place better recreates 18th-century tavern life as evidenced by servers in period attire (in The Ordinary dining room), traditional Colonial Virginia cuisine (think Southern fried chicken and hickory smoked pulled pork) and period-inspired dish and glassware. Take a self- guided tour which includes interpretations on drinking, gaming, dining, sleeping and entertainment to give an idea of the experiences of the travelers who made the Michie a common stop on westward adventures.

In keeping with historic surroundings, the Ivy Inn stands at the former site of the Faulkner House, an estate named for William Faulkner, a Southern aristocrat and distinguished University of Virginia “writer in residence.” The home that houses today’s seasonally-driven restaurant was built around 1815. In 1973, the Ivy Inn restaurant was established with a mission to provide the community and visitors with a richly historical and elegant atmosphere for dining. It should come as no surprise to find a fabulous French restaurant in Jefferson’s city —he was the American Minister to the Court of Versailles after all. Fleurie has earned its stellar reputation here over the past nearly 20 years. The chef’s tasting menu is the best way to savor the spoils of local farms, though a la carte options will not disappoint (and the desserts are outstanding). Regularly recognized by Wine Enthusiast, the impressive wine list leans heavily French as expected but to parallel its menu, is locally driven.

What to See & Do

With most roads in C'ville leading back to Jefferson, start with the obvious: Monticello. You’d be foolish to skip the David M. Rubenstein Visitor Center as it will explain why this historic mountaintop estate is more than just the four-decade evolution of Jefferson’s vision but also, a place where his thoughts on life and liberty developed.

Learn more about the experiences of the enslaved people who lived and labored on the Monticello plantation on the Slavery at Monticello guided outdoor tour (included with admission). For a more in-depth, interactive experience, take the Hemings Family Tour, which explores the site through the lens of the Hemings family — one of the best documented enslaved families in the U.S. The tour includes dialogue about race and the legacies of slavery in our country in a small group setting (the tour is not recommend for children under 12).

Photo by Sanjay Suchak, Courtesy of Charlottesville Albemarle Convention & Visitors Bureau

If you’re on this website, then the self-guided Monticello Artisan Trail is right up your alley. This network of craft artisans throughout Nelson and Albemarle County includes studios, galleries, markets and agri-artisan farms in addition to the events and workshops related to their craft. Fine furniture, ceramics, pottery, wineries and more make up this diverse collective. If the calendar allows, check out the Artisans Studio Tour held annually on the second weekend in November. 2019 marks the tour’s 25th year and will feature more than 40 artisans in more than 20 working studios.

Photo by Lori Coleman Courtesy of Charlottesville Albemarle Convention & Visitors Bureau

Considered the birthplace of American wine, the Charlottesville area is home to 35 wineries within a 30 miles radius which comprise the Monticello Wine Trail. Here you’ll find a spectrum of producers and varietals, many of which have been highly recognized. Though the region is Bordeaux-leaning, there’s no shortage of phenomenal whites, Rieslings and ice wines. Pro tip: book a driver-led tour in advance. There are a number of great companies including Monticello Wine Tour and Coach Co. and Wish Wish Wine Tour which will not only make the most of your wine-hopping time, but will get you there safely.

Andrea McHugh

Andrea E. McHugh is a media manager, content creator and freelance writer specializing in lifestyle topics including travel, fashion and beauty, homes, weddings and wellness. She’s a regular style correspondent for The Rhode Show on WPRI (CBS) Providence and contributing writer for ArtisansList.com.

She served as an editor for Newport Life and Newport Weddings magazines and her work has appeared in Family Circle, the Hartford Courant, Classic Boat Magazine, Baltimore Magazine, Cape Cod Home, Daily Candy, Design Sponge, Northern Virginia Sun Gazette newspapers, Ocean Avenue, New England Gala Weddings, Providence Monthly and additional regional, national and international print and digital publications.

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