Wine Roads of Virginia

The wine-rich region surrounding Charlottesville makes for a romantic weekend respite.



You’ve got two days, a date on your arm and a desire to explore wine country, but nowhere to stage a romantic tête-à-tête? With scenic, gently sloping hills, curvy, one-lane country roads and winery after winery—not to mention fascinating historical sites, plush accommodations and fantastic food—the Monticello AVA in central Virginia is an ideal destination for those seeking a wine-centric weekend getaway.

Where to Stay

Splurge on a well-appointed room (or private cottage suite) with personalized butler service at the Inn at Willow Grove. Formerly a plantation, this luxurious landmarked property has been gorgeously restored and features 14 oversized rooms and suites that boast heated marble bathroom floors, soaking tubs, fireplaces and L’Occitane beauty products. The lush 40-acre property invites exploration à deux—the rolling green hills are dotted with willow trees and lined with walking trails. Other endearing touches on the property include porches with rocking chairs, reflecting pools and outdoor fire pits. Each morning, guests of the Inn are greeted with French-pressed coffee and freshly made beignets delivered to their door, along with the daily newspaper. Other standouts for stylish accommodation include the stately Keswick Hall and charming Boar’s Head Inn.

Day One

Head into Richmond (a two-hour flight from New York) and rent a car. A GPS system is essential—otherwise, you’ll find yourself hopelessly turned around in the countryside. Unless roaming off the beaten track is on your agenda, arm yourself with a detailed map of the region and plot each winery on your hit list.

Start your first day with a tour of historic Montpelier—the recently restored residence of former President James Madison and his wife, Dolley, who was renowned for throwing lavish dinner parties, subsequently inspiring the title of “First Lady.” Located in Orange, Virginia (about 30 minutes from Richmond), Montpelier offers unparalleled views of the Blue Ridge Mountains and rare glimpses into the lives of our nation’s forefathers. A slave cemetery, Civil War encampment site and 200 acres of old-growth forests are among the property’s attractions. Foodies shouldn’t miss the fascinating 19th-century cooking demonstration held on the mansion’s north lawn.

After exploring Montpelier, take a short drive to Barboursville Vineyards—run by Italy’s Zonin family—and tour the beautiful, 830-acre property (which includes the ruins of a manor designed by Thomas Jefferson for Virginia governor James Barbour). Make an appointment beforehand and do it right. After swirling and sipping Barboursville’s well-known Octagon wines in the charming barrel-aging room with convivial vintner Luca Paschina, sit down for an elegant Italian lunch at Palladio restaurant next door—the three-course lunch with wine pairings is a great way to refuel midday. Rustic, Northern Italian dishes include house-made sausages and charcuterie, penne with braised rabbit and quail marinated in red wine.

Later that afternoon, set your course for Keswick Vineyards, where you can try multiple pours for $5 ($8 with souvenir glass) in the main tasting room, or buy a bottle of the vineyard’s award-winning Viognier and take a blanket (provided by the vineyard) to picnic on the property’s beautiful, forest-like grounds. Rustic picnic tables are another option for spreading out and enjoying the scenic countryside and a glass of vino in the late afternoon. And each Sunday, four-legged friends are welcome to join along in the fun.

For dinner, head to Vintage, an upscale restaurant located below the Inn at Willow Grove. Dishes on offer here reflect local ingredients and Southern specialties, including goat cheese gnocchi with sage cream and balsamic-grape reduction, muffalata bites and crab cakes with gingered cream corn.

Day Two

It would be difficult to fully appreciate Virginia wine country—particularly Monticello—without making a stop at Thomas Jefferson’s historic hilltop estate, for which the AVA is named. After a guided tour of Monticello (monticello.org), Jefferson’s fascinating plantation, stop by the recently restored wine cellar below the mansion. Influenced greatly by his time spent in Europe, Jefferson was an avid wine drinker—his cellar contained bottles from the best chateaus in France (he also collected wines from Spain, Italy, Hungary and Portugal) and he took extensive tasting notes that survive to this day. The cellar features a dumb waiter that was designed specifically for replacing empty wine bottles, enabling Jefferson to replenish wine in his dining room (located directly above the cellar) without the aid—or interference—of his servants.                       

Jefferson famously attempted to establish Vitis vinifera in Virginia, planting about 200 acres of grapevines less than one mile away from Monticello in the late 1770s. And while these plantings did not flourish, Jefferson Vineyards succeeds in producing wine on the original site today. Located less than a five minutes’ drive from Monticello, stop by Jefferson Vineyards to sample a variety of wines (for a nominal $5 tasting fee), and take a free tour of the lovely grounds. You may even catch a glimpse of local legend (and associate director of gardens and grounds at nearby Monticello, but also vintner and wine consultant) Gabriele Rausse, widely considered to be the “father of Virginia wine.” (Rausse recreated Jefferson’s historic vineyard in 1984, grafting and planting 22 vinifera varieties on the same hillside.)           

Before your next winery stop, grab a bite to eat at the charming Michie Tavern, which has been serving suds and Southern fare since 1784. Taking visitors back in time to the 18th century, diners can dance a colonial reel with costumed servers, play tavern games and indulge in hickory-smoked pork, baked chicken, stewed tomatoes and other dishes created from colonial-era recipes.                    

Finish your day with a stop at Blenheim Vineyards. Owned by musician Dave Matthews, this dog-friendly and eco-conscious winery features a chalet-style tasting room built from reclaimed wood (in the summer, large skylights render electricity unnecessary to light the space). Sit at one of several large tables and take in views of the barrel room below. Seen through dramatic glass floors, visitors can catch glimpses of winemaker Kristy Harmon hard at work. The screw top-only wines at Blenheim are made to be sipped young, and with distinctive labels designed by Matthews himself, make for an excellent souvenir from your Virginia wine weekend.

Behind the scenes at King Estate.Other Activities

If time permits, take your date on a romantic horseback trail ride at Oakland Heights Farm or get lost together in the one-acre Garden Maze featuring eight-foot-tall hedges, hidden tunnels and a lookout tower. Fill up a picnic basket at Forest Lakes farmers’ market, where tasty, artisanal food items like Farmstead Ferments pickles, cheeses from Mountain View Farm and produce from Davis Creek Gardens are sold. If more wineries are on your agenda, consider visiting vineyards in nearby Crozet, home to King Family Vineyards, White Hall Vineyards in White Hall and Pollak Vineyards in Greenwood are other worthwhile options.

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