Things to Do in Charlottesville

A visit to Virginia’s wine country is a trip back in time to when Thomas Jefferson planted the seeds of America’s first vineyards. Jefferson Vineyards, wanting to continue the Founding Father’s dream of wine in the region, offers visitors a rustic spot to sip chardonnay, meritage, and petit verdot while taking in Virginia’s lush landscape.

The historic location of Jefferson Vineyards, just 1 mile (1.6 kilometers) south of the historic Monticello estate, offers guests a well-rounded experience to learn about American history and Virginia wine. See how Jefferson and Italian viticulturist Filippo Mazzei imagined the state’s vineyards as you tour the winery, taste its varietals, and admire the beautiful views of Monticello and beyond. You can also hop on a private tour of the Monticello Wine Trail to explore other wineries in the Charlottesville region and learn how the unique climate of Virginia affects the wines. If traveling independently, you can spend the day exploring Jefferson Vineyards and other wineries along the Monticello Wine Trail, or visit Monticello itself and the University of Virginia.

Jefferson Vineyards, located on the eastern side of Monticello, is a 10-minute drive from Charlottesville. If you’re coming from farther afield, take Route 29 from Washington DC or I-64 from Richmond. The Monticello Wine Trail is accessible only by car or organized charter bus.

The vineyards are open daily from 11am to 6:15pm; see the website for seasonal closures. Fall is the best time to visit Virginia, when the weather is crisp and the trees explode in hues of yellow, orange, and red.

Convinced by other Founding Fathers, Filippo Mazzei ventured across the Atlantic with European vines to plants America’s first winery on lands donated by Thomas Jefferson. The two neighbors aspired to produce some of the world’s greatest wines in the New World. When the American Revolution began in 1776, Mazzei enlisted as a private with the colonists—and soon after, wine production seized up until the 1980s.

Drink up incredible scenery along with award-winning wines during a visit to Trump Winery, nestled into the foothills of Virginia’s idyllic Blue Ridge Mountains. The winery sits just a few miles from Monticello, the historic home of Thomas Jefferson, and James Monroe’s Ash Lawn-Highland. With 165 acres of grapes across the 1,300-acre estate, Trump Winery clocks in as the largest vineyard in Virginia. Its wines are critically acclaimed, especially the sparkling varieties—the 2007 Trump SP Reserve is the highest-rated wine in Virginia—while the Sauvignon Blanc and Chardonnay rate highly as well.

Located along the Monticello Wine Trail in Virginia, Blenheim Vineyards is a family-owned operation dedicated to making high-quality wines that reflect the climate of the surrounding piedmont landscape. The winery’s two vineyard sites produce chardonnay, viognier, cabernet franc, petit verdot, and cabernet sauvignon varieties.

The Blenheim Vineyards winery was built in 2000 using environmentally friendly practices, such as offering white and red house wines on tap. It provides an intimate setting for wine tastings with large windows looking over the sea of green vines and paneled glass floors offering views to the production below. 

You can visit the winery on your own—spend the day visiting several wineries or go apple picking in the nearby orchard before stopping to Blenheim. Alternatively, book a private behind-the-scenes wine tour to explore Blenheim Vineyards and other wineries in the area—and leave the driving to someone else.

Blenheim Vineyards is located 20 minutes southeast of Charlottesville, just off of VA-20 South. Take Route 29 from Washington DC or I-64 from Richmond to get to Charlottesville. The Monticello Wine Trail is accessible only by car or organized charter bus.

The best time to visit Blenheim Vineyards and the Monticello Wine Trail is during the fall when the leaves begin to change color. Fall in Virginia offers crisp days and wonderful leaf peeping, perfect for sipping wine and enjoying the surrounding landscape.

Blenheim Vineyards is built on a historic estate once owned by the Secretary of the Colony of Virginia, John Carter, during the 1700s. It is still home to a few 18th- and 19th-century buildings such as a school-chapel and library. In the year 2000, folk singer Dave Matthews purchased the estate and transformed it into the winery you see today.

One of the most awarded breweries on the East Coast, Virginia’s Starr Hill is the largest independent craft brewer in the state. The regional brewery distributes mostly in the mid-Atlantic and Southeast, and stays close to its historic roots. Founded in Charlottesville's Starr Hill Music Hall in 1999, live music plays a big role in the brewery's story.

Though the facilities have since moved to a larger industrial property, Starr Hill Brewery still has a stage for performers and now hosts food trucks every weekend on its patio area. The brewery has been recognized as a leader in the growing craft beer scene, with 16 different beers on tap—and many of them award-winning.

Tour this brewery and many more on a private or hop-on, hop-off bus tour of Crozet's breweries and wineries, which include beer tastings and round trip transportation from Charlottesville.

The Virginia land on which Keswick Vineyards stands was handpicked by the Schornberg family, who still owns and operates the estate today. Spread across 400 acres, a historic mansion serves as the center point for the estate. The scenic surrounding vines produce some of the area’s best grapes, which are then hand picked and hand sorted to ensure top quality. Their process emphasizes quality ingredients and a minimalist approach to winemaking. As such, the grapes undergo very little manipulation, using natural yeast and no filtration.

The vineyard’s location allows for nice views of the Blue Ridge Mountains. Tours give valuable insight into the winemaking process and the unique geography of the area. The tasting room has a relaxed feel, with the courtyard and porch open as weather permits and games and activities typically present. The winery is known for producing award-winning wines; their Chardonnay, Viognier and Heritage wine are particularly tasty.

Thomas Jefferson founded the University of Virginia in 1819 to promote discussion, collaboration, and enlightenment through higher education. Today the UNESCO World Heritage Site is considered to be a “public Ivy,” on par with the Ivy League institutions, making it one of the top schools in the nation serving roughly 25,000 students.

Thomas Jefferson established the Academical Village—which includes the Rotunda, the Lawn, the Pavilions, and the Gardens—where students and faculty could cohabitate to foster better academic exchanges. Free guided tours of the Lawn and the Rotunda are offered throughout the year to get a feel for what life was like for students and faculty in the early days. Most tours discuss the history of Charlottesville, from its plantation days to the Civil War that ripped through the southern state to the present day. Some private Civil War tours of central Virginia stop by the university, the former headquarters of the Confederate General Hospital.

The University of Virginia is located in the heart of Charlottesville, about two hours southwest of Washington DC. To reach campus, drive along Route 29 from DC or I-64 from Richmond.

The university and its grounds are open throughout the year for tours and visits. It is best to avoid the school during Thanksgiving, Christmas, and Spring Break, when there are more closures and fewer students milling around the grounds.

Jefferson’s vision for the University of Virginia can still be seen today on tours of the original grounds. Though the Rotunda is no longer used as a library, it is still the heart of the university and is modeled after the Pantheon in Rome. The structures that flank the Lawn are pavilions and student houses occupied by the most accomplished fourth-year students and honored faculty. The Gardens, once used for growing food, are now ideal for relaxing strolls.

Set in an old schoolhouse on ten acres of Virginia farmland, Nelson County's Wild Wolf Brewing Company is as beautiful a place to visit as it is a popular spot to drink. With a wraparound porch and views of the mountains, the brew house serves its unique craft beers in a picturesque, Southern setting, and features seasonal offerings as well as a pilsner, ale, and stout influenced by the brew master's time in Germany and Chicago.

Go behind-the-scenes on a brewery tour, or enjoy a cold one under the shade of Siberian Elm trees in the beer garden. Here, you can enjoy the brewery's grounds or have a bite to eat at its restaurant, which is known for using local ingredients and specializing in hickory smoked meats.

Revered for its hospitality, the brewery is a great stop for thirsty visitors, and often features live music and outdoor games.

The vineyards at Barboursville surround an 18th century estate that once belonged to James Barbour, the governor of Virginia (for which the area is named.)  They are inspired by Thomas Jefferson’s nearby Monticello estate, who in fact designed the stately mansion.

The grounds were once farmland deemed unworthy of making wine, until an Italian man purchased the property and brought with him his family’s winemaking legacy. Wines are still created in a European style. Today the star of the vineyards is undoubtedly its Cabernet Franc, served both in its tasting room and with culinary pairings in its Library 1821 building.

Other varietals depend upon the year, though the vineyard has made Nebbiolo, Sauvignon Blanc, Viognier, and others throughout the years. Tours grant insight into the history of the estate and the winemaking process, as well as the story of the vineyards’ signature wine.