A trip to this Virginia city offers history, horseback riding, dining and shopping, too
Try as he could, Thomas Jefferson never managed to encourage vitis vinifera, aka grapevines, to grow at his beloved Monticello.
That was unfortunate, since the Founding Father so enjoyed his vin that he yearly imported from France 600 bottles from outstanding − and expensive − producers such as Chateau Lafitte. His taste for the best fruits of the vine undoubtedly added to the substantial debt he incurred.
Jefferson may have experienced grape-growing woes, but as the wine connoisseur of his age, he paved the way for Virginia to become the birthplace of American wine.
Winemakers in Jefferson’s neck of the woods long ago cracked the code for good wine and the Charlottesville wine culture is thriving with an energy and joy T.J. would have appreciated. With its handsome hills and stunning valleys, it is an area picture perfect for vineyards, and today’s wine aficionados not only can enjoy the fruits of the vine, but they can stay amidst the glory of the vines, exploring on horseback some of the more than 40 vineyards that dot a 20-mile radius from Charlottesville.
While the region does not produce enough wine to realistically distribute outside its borders, winery hopping is a passion that attracts visitors to the Monticello Wine Trail every day, every season, from everywhere.
On Tuesday mid-afternoon in early fall, while the rest of the world worked, people packed the Eastwood Farm and Winery tasting room in Charlottesville.
The 77-acre property was the dream-come-true for attorney Athena Eastwood, recognized as a 2021 Trailblazer by the “National Law Journal” for her work with sustainable agriculture and renewable energy. In 2016, she purchased the original 1800’s farm of Thomas Jefferson’s builder, John Dunkam, with the vision of starting a farm winery on the property. Daughter Hannah runs the family business, aided by 6-year-old daughter, Josephine.
Out of five wines Eastwood entered in the 2021 statewide Governor’s Cup wine competition, two received silver medals (Tall Tails White Blend and Raspberry Rose) and the other three went bronze (2019 Tall Tails Merlot and 2019 Tall Tails Chardonnay, plus 2019 Meritage).
Family-run wineries such as Eastwood’s offer unique opportunities to enjoy good − albeit not inexpensive − wine in surroundings that beg for return visits.
Come Sundays during the summer, families pack their cars and head to King Family Vineyards in the heart of the Monticello AVA. This is not just wine country, but also horse country, and for the King family, horses mean polo ponies, as in the 54 that call the place home. The vineyard features a full-fledged playing field where visitors can witness the Sport of Kings while sipping one of King’s multiple award-winning wines. One of USA TODAY’s “Top 10 Winery Tours,” King Family Vineyards merits multiple visits, and none of these should be rushed.
Like Eastwood, King is family-run. Texan transplants David and Ellen King planted the original vines. Along with a passion for good wine, the late patriarch brought his beloved sport of polo. Ellen King continues working at the winery, helping sons Carrington, Stuart and James carry on her husband’s hands-on legacy.
“My father always said that the most important thing in the vineyard is the owner’s shadow,” said James King.
Less than a half hour away from the Kings and their ponies, Keswick Vineyards is also run by a family, which in this case includes winemaker Stephen Barnard, son-in-law to Al and Cindy Schornberg, who in 1999 planted the initial 32 acres. Barnard honed his winemaking chops in South Africa and has done well for the family winery, winning several Virginia Governor’s Cups, double gold medals at the San Francisco International Wine Competition and Atlanta International Wine Summit’s “Best White Wine in America” for the 2002 Viognier Estate Reserve.
“At the end of the day, we’re farmers,” he said.
He can sympathize with Jefferson’s winemaking trials and tribulations, but believes Virginia, and in particular Charlottesville, have much to offer wine-wise.
“There are easier places in the world to grow grapes, but we can make terrific wine,” he said.
While horses are part of the atmosphere at King, mini-golf is the game at Keswick. Many Charlottesville vineyards add such extra pleasant distractions to a tasting room visit.
And while tasting room visits are nice, for the ultimate vineyard tour with a unique perspective, connect with Indian Summer Guide Services, for horseback tours around several area vineyards.
Of course, wineries and vineyards are a small part of the picture of Charlottesville. At the epicenter is Monticello, always serene, always beautiful and always ready to share something new.
If your last visit was many years ago, you will notice the experience now begins at the David M. Rubenstein Visitor Center and Smith Education Center, which serve as the 21st-century gateway to Jefferson’s timeless mountain getaway. Multiple components prepare guests for their trips to the historic mountaintop through dynamic content presenting fresh perspectives on Monticello and the enduring significance of Jefferson’s life and ideas.
Jefferson’s relationship with Sally Hemings, once a subject largely skirted, is now frankly discussed. “It’s complicated,” as one tour guide noted.
Visitors can even come face-to-face with a living, breathing Jefferson, portrayed by veteran actor Bill Barker, recognized as the foremost interpreter of our nation’s third president. Tuesday through Saturday, Barker channels his impressive inner Jefferson, bringing a deep and nuanced portrayal of the brilliant, complex man who wrote that “all men are created equal” yet kept slaves throughout his life.
Michie Tavern is another Charlottesville must-do, particularly since the drive to Monticello takes travelers past the 1784 tavern, moved 17 miles in 1928 to its current location a half-mile from Jefferson’s home.
Midday dining, patterned after the southern tradition, features glorious examples of comfort food, from Southern fried chicken and hickory-smoked pulled pork to black-eyed peas seasoned with country ham and cornbread. There is wine, of course, generous portions served in Colonial-style tin cups to slake thirst and to sip by a roaring fire during winter months.
The Downtown Mall is a historic eight-block pedestrian artery running through the heart of Charlottesville. Here you will find eateries and performance venues such as the boisterous Whiskey Jar, plus boutiques, bookstores and more.
Art is presented in funky hubs that include IX Art Park, a public, non-commercial, interactive space where visitors can wander night and day. Events from salsa dancing to music festivals to martial arts classes happen here.
Eating in Charlottesville is never boring. Dairy Market, located in the historic Monticello Dairy Building downtown, brought the National Food Hall Revolution to Charlottesville. A cornucopia of food options scratch any foodie’s itch for an authentic culinary experience, from Korean to Southern, like Angelic’s Kitchen with its fried fish dipped in a unique southern-style breading and complemented with sides such as collard greens and sweet cornbread.
When it comes to places to stay, all the usual homogenous chains abound, but there is plenty of singularity in lodging options. Lodging can be quirky, as in Quirk Hotel, a hotel/art gallery combination just a few blocks away from Downtown Mall. The boutique hotel’s crowning glory is a rooftop bar with a glorious view of the city and the surrounding mountains.
Accommodations can also be extremely cozy, as with the Townsman, right on Downtown Mall and boasting all of four rooms, so you can rent the whole place if you wish.
If expansive is the goal, the 600-acre AAA Four-Diamond Boar’s Head Resort, owned by the University of Virginia Foundation, excels in southern hospitality with a variety of world-class recreational activities spread over considerable acreage.
You can even opt for a sip and stay vineyard vacation at the four-star Albemarle Estate, or for a more intimate experience, at Meriwether Springs Vineyard, home to a four-bedroom/three-bath house that sleeps up to 14. At Arcady Vineyard, lodging guests are treated with a glass of wine at check-in, plus a wine fridge stocked with a bottle of sparkling wine. The Inn at Stinson Vineyards features four suites, all with breathtaking views of the vineyards.
Yep, the wine is fine in Charlottesville, as is the rest of the place.