In 1773, Thomas Jefferson planted sangiovese vines at Monticello, hopeful he could reproduce the European wines he loved on his own hilly terrain. While his efforts ultimately failed, today Virginia is home to more than 300 wineries, where both Old World and native varieties flourish. This trip takes you through the heart of the state’s wine country, beginning with a flight into Washington, D.C., where you’ll rent a car and then sip your way across the gentle hills of central Virginia—alternating designated drivers each day—before eventually flying out of Charlottesville.
WASHINGTON, D.C. TO WASHINGTON, VA
Leave the Beltway traffic behind and make your way to “little” Washington, a five-by-two-block town in the foothills of the Blue Ridge Mountains that 17-year-old George surveyed himself in 1749. The day’s 65-mile drive includes a stop in horse country, where painted fences and low stone walls frame miles of pastures. Expect to get stuck behind a slow-moving equestrian trailer, and embrace it.
Middleburg | Established in 1787, this picturesque small town is known as the nation’s “horse and hunt” capital. Many original buildings still stand, including the Red Fox Inn & Tavern, a favorite destination of Jacqueline Kennedy Onassis. The inn’s namesake animal is everywhere in Middleburg: on street signs and garden sculptures, on wine glasses at the Fun Shop boutique, and in antique oil paintings at the National Sporting Library & Museum. Stop for lunch at King Street Oyster Bar, which offers at least 12 varieties of oysters, many from the Chesapeake Bay, along with tuna tacos, ceviche, and lobster rolls—ideally paired with a glass of viognier from nearby Breaux Vineyards.
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A short drive from Middleburg is RdV Vineyards, known for its award-winning Bordeaux. Appointment only tastings include tours of the wine caves.
White Moose Inn | Set among historic cottages in the tiny town of Washington, this eight-room inn is refreshingly minimalist. Its marigold-yellow front door pops against the painted white exterior, and rooms exude modern countryside charm through whitewashed decor, black-and-white photographs, and tiny bedside glass jars of M&Ms. Happy hour features selections from Madison County’s Early Mountain Vineyards (which you’ll visit tomorrow), best enjoyed by the stone firepit. Or borrow a bicycle for a pre-dinner ride around the quiet, shady streets.
Patty O’s Cafe and Bakery | The acclaimed Inn at Little Washington is the first and only restaurant with three Michelin stars in the D.C. region. While chef Patrick O’Connell’s five-course menus, known for being both serious and whimsical, are certainly worth the splurge ($328 per person), his newest restaurant, Patty O’s, offers many of his signature dishes in a more casual setting across the street. Staples include the grilled pork chop with apples and sauerkraut, the towering half-pound local Wagyu burger, and the showstopping homemade butter pecan ice cream, drizzled with warm caramel and served in a chalice. Look for several Virginia offerings, such as Blenheim’s On the Line red blend, on the rotating wine list.
WASHINGTON, VA TO BARBOURSVILLE, VA
Today’s 85-mile journey starts with an early drive to Shenandoah National Park, through farmland and the historic small towns of Sperryville and Madison, and ultimately to your resting spot for the night, Barboursville Vineyards. Along the way, stop at roadside markets like Beech Spring Gift Shop, run by the same family for more than 80 years, and the Corner Store, a gourmet market (and former 1840s butcher shop) in Sperryville with everything you need for a picnic lunch on the park trails.
Shenandoah National Park | Use the Thornton Gap entrance and drive south on Skyline Drive, stopping at Jewell Hollow Overlook for a picnic in the adjacent grassy area or on one of the massive boulders. If you’re feeling more active, continue to Hawksbill Summit for a short (1.6-mile) but steep route to the park’s highest point (4,051 feet). The walk across the rocky terrain can be intense, but at the top, the Shenandoah Valley appears like a patchwork quilt of greens and golds. Skyland resort is also nearby, a worthwhile stop for blackberry ice cream pie.
Early Mountain Vineyards | Change out of your hiking gear for a visit to this winery’s sprawling limestone-and-brick mansion. Owned by AOL cofounder Steve Case and his wife, Jean, the cavernous space feels elegant yet warm, with a central fireplace, plush cream sofas, and farmhouse tables leading to a veranda overlooking a meadow. No matter where you sit, order a glass of Eluvium, a red blend with deep, layered notes of cocoa, cedar, and black cherry.
The 1804 Inn and Cottages at Barboursville Vineyards | Founded in 1976 by the Zonin family, one of Italy’s largest wine producers, Barboursville is one of the region’s most award-winning wineries. Any distinction between Virginia’s Piedmont and Italy’s Piemonte blurs as you pass the weather-worn white fences into the 870-acre estate, where cows wander the hilltops, church bells chime in the distance, and the ruins of a mansion designed by Thomas Jefferson for Governor James Barbour beckon in a nearby field. Skip the main tasting-room crowds and stop for a flight (reserved in advance) in Library 1821, which pours both current releases and older vintages. Then check into the historic inn, where suites awash in luxurious Italian linens and fine antiques are surpassed only by their welcoming outdoor spaces—expansive balconies with Adirondack chairs and gardenside patios perfect for sipping a plummy Cabernet Franc Reserve.
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The notable Rappahannock wine region includes Gadino Cellars, where bocce is part of the Italian-inspired atmosphere, and Little Washington Winery, located on the outskirts of Shenandoah National Park.
Palladio at Barboursville Vineyards | You’ll feel like you are dining in a Tuscan farmhouse during this four-course, wine-paired feast. Chef Michael Clough creates seasonal Northern Italian dishes reflecting the abundant local produce: housemade ricotta cavatelli with pancetta and locally foraged mushrooms, for example, or grilled lamb chops with local kale and butternut squash.
BARBOURSVILLE, VA TO AFTON, VA
Today’s itinerary begins with history and ends with dinner among the vines. The 55-mile trip traverses the edge of Charlottesville and the Monticello Wine Trail, past farms, beautifully manicured estates, and so many vineyards you’ll lose track.
Monticello | Thomas Jefferson’s expansive home and grounds are as well-maintained as ever, and the recently expanded Slavery at Monticello tour, offered on the hour, illuminates a lesser-known part of Jefferson’s legacy. Of particular note are the stone wine cellars, where Jefferson stored the 400 bottles he had shipped from France and Italy each year. Consider taking a walk through the surrounding native hardwood forest; the Saunders- Monticello Trail is a series of elevated wooden paths that hug the mountain and offer a refreshing start to the day.
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The Monticello Wine Trail includes more than 40 wineries within a 25-mile radius of Charlottesville, including Blenheim Vineyards, owned by musician Dave Matthews, who paints many of the wine labels.
Gabriele Rausse Winery | A short drive from Monticello (and passing James Monroe’s estate, Highland), this boutique winery is hidden beneath a canopy of trees. Two mild-mannered yellow labs welcome guests to the intimate outdoor tasting area and small wood-and-glass tasting room. Rausse, originally from Vicenza, Italy, is hugely influential in Virginia wine; he was the original winemaker at Barboursville and has consulted on many vineyards in the state. Here, flights of four wines are presented in small apothecary bottles and may include selections from “Wine from the Woods,” made without added sulfites.
SIP & SNACK
Pippin Hill Farm & Vineyards | Stop here for stunning views of the Blue Ridge in addition to farm-fresh food and wine. Reserve a table on the veranda, where a wine tasting complements shared plates such as charcuterie and local cheese with veggies from the kitchen garden just a few feet away. Wander among the vines and gardens with a glass of petit manseng (Virginia’s equivalent of the perfect French white) and take a peek in the greenhouse, which harbors organic seedlings for the next season, and the custom chicken coop, complete with flowering window boxes, for the clucking “Ladies of Pippin.”
The Farmhouse at Veritas | Staying at this 183-year-old bed and breakfast, surrounded by mountains and grapevines, is like staying with a dear friend who happens to be a professional chef. Rooms are comfortable and serene, with elegant details like silk curtains and wide-planked wood floors. “Wine hour” is at 5 p.m. and includes a short walk to the wraparound porch for an amuse-bouche and semi-private tasting of Veritas wines, such as the light-bodied Red Star blend.
The Farmhouse at Veritas Restaurant | Dinner is an elegant four-course affair served in a glass-walled cottage in the garden, nestled so close to the grapevines it’s possible to see the occasional insect hopping leaf to leaf. Tables are set with flowers from the garden, and chef John Meiklejohn prepares seasonal dishes such as roasted pork belly with pickled cherries and a truffled cauliflower soup with lemon paired with Veritas sauvignon blanc. The sparkling-wine breakfast is equally pleasant, with homemade croissants, your choice of sweet or savory entree (order the vanilla crepes), and if you’re lucky, the charming sight of a small tractor trimming the vines.
AFTON, VA TO CHARLOTTESVILLE, VA
It’s the last day of your trip, but depending on your timing, you might wish to explore before heading to the airport. Take a closer look at the vineyards on horseback, wander through an apple orchard, or head to downtown Charlottesville for lunch and a stroll.
Scenic horseback ride | Indian Summer Guide Service offers guided rides at Veritas, King Family Vineyards, and Keswick Vineyards, all within easy reach of Charlottesville. Well-trained quarter horses take guests on a relaxed tour through the vines and meadows and across small streams, ending at the tasting room for one last glass.
Chiles Peach Orchard | This family-owned orchard bursts with more than 20 varieties of apples each fall. Pick a few yourself or take home a selection of Virginia Gold and Albemarle Pippin from the farm market, along with their famous apple-cider doughnuts.
Charlottesville’s Downtown Mall | a pedestrian-friendly promenade adorned with twinkling lights and baskets of flowers, offers a host of eateries, most with outdoor seating. Tilman’s is a worthy choice for small plates, charcuterie, and local cheeses. If you have a later flight, Red Pump Kitchen, owned by the team behind Pippin Hill, opens at 5 p.m. for dinner.
This article appears in the Fall/Winter 2022 issue of Southbound.