Virginia Wine Country produces wines that are as beautiful and diverse as its landscape — and, best of all, it’s just a five-hour drive from New York City.

Located in the heart of the mid-Atlantic, Virginia is the first recorded wine-growing area in the country (beginning in Jamestown in 1607) and now, 400 years later, with over 300 wineries spread across the state, there’s a wine for every palate.

To help you plan an ideal weekend in Virginia Wine Country, we’ve prepared mini-itineraries for three key wine regions —Northern Virginia, Central Virginia and the Shenandoah Valley — highlighting some of the best food and drink destinations (plus a few things to do in between).

NORTHERN VIRGINIA

From the Vine

Located just 50 miles west of Washington, D.C., the city of Middleburg has its own designated American Viticultural Area (AVA), delineated in the north by the Potomac River, with the Blue Ridge and Bull Run mountains defining its east, west, and southern borders. Here, there are more than 20 wineries. Don’t skip Boxwood Estate Winery, which spearheaded the movement to get the AVA recognized, and here you’ll find wines made in the Bordeaux tradition and expressed in a uniquely Virginian way. Another Middleburg must is Chrysalis Vineyards, which prides itself on its Norton wines — made from America’s oldest native grape variety — that you can pair with farm-fresh cheeses made on-site.

Other notable wineries in Northern Virginia include: Breaux Vineyards, a family-owned 404-acre estate in Loudoun, which features a pink-roofed tasting room with an array of dry white, red, and rosé wines at the ready; Bluemont Vineyard, nestled on the first ridge of the Blue Ridge Mountains, offers a four-course Chef’s Table tasting on Friday and Saturday evenings; and 868 Estate Vineyards, which took gold in the 2020 Virginia Governor’s Cup for its 2017 Vidal Blanc.

Where to Dine

The Red Fox Inn is situated between the Bull Run and Blue Ridge mountains in Middleburg, and was established in 1728. Here, four-course seasonal menus and Virginia wine pairings are served on a charming terrace. In the fall, toasted pear crostini might meet its match with a NV Extra Brut from Thibaut-Janisson Winery, while a butternut squash bisque could be complemented by Greenhill Vineyards’ 2019 Viognier. Book the inn’s cottage suite, with its own courtyard, for a sublime fall weekend in hunt country.

If a bed & breakfast is more your style, stay at The Ashby Inn, located in Paris, Va., which dates back to 1829. The inn has won a Best of Award of Excellence from Wine Spectator as well as Diner’s Choice – Best Scenic View, Notable Wine List, & Contemporary American from Open Table, which is no real surprise given its collection of 250 wines from around Virginia and the world.

Then, head to Marshall to dine at the award-winning Field & Main, set in a 200 year-old house. There, on the sunny patio, you can enjoy chef Neal Wavra’s hearth-cooked dishes, like ember-roasted wild coho salmon or pork belly a la plancha, and an impressive list of wines from Virginia and beyond, including a red or white “mystery” glass that’s half off if you can guess the grape.

What to do

When you’re ready to take a break from wine (for now), Northern Virginia is a mecca for history buffs, with Arlington National Cemetery and George Washington’s Mount Vernon (which also happens to have a recreated, fully functioning distillery with its small-batch whiskey available for purchase).

SHENANDOAH VALLEY

From the Vine

Further west is the Shenandoah Valley AVA — the state’s largest — with a drier climate and rocky soils. Here, you’ll find Chardonnays, Cabernet Sauvignons, Merlots, and Cabernet Francs, as well as hybrids like Chambourcin and Traminette.

One must-visit destination in this region is Glen Manor, a fifth-generation farm that focuses on “wines with a sense of place.” There, the vines grow on steep slopes, and they specialize in estate-grown Sauvignon Blanc, Petit Manseng, and red Bordeaux blends and varietals. Be sure to try the ripe-berried Hodder Hill, which took home a gold medal in this year’s Governor’s Cup.

For small-batch wines and mountain views, head to family-run Bluestone Vineyard in the western Shenandoah Valley and try the award-winning Blue Ice, which is reminiscent of Germany’s eiswein. Another winning stop is Ox-Eye Vineyards, named for the ox-eye daisies that blanket its landscape in the summer. Its tasting room is in the Historic Wharf District in downtown Staunton, where you can sample a variety of food-friendly reds and whites, including the Lemberger and Riesling wines.

Where to Dine

Good food doesn’t have to be fancy, and The Shack is our No. 1 pick for quality cuisine sans snobbery. At this Staunton eatery, the owners combine local flavors with their mountain roots and Eastern European Jewish heritage to offer a taste of what they’ve dubbed the “Schmaltzy South.”

Take a bottle of Shack Sauce with you when you leave.

What to Do

For a fresh-air fix, head to the 200,000 gorgeous acres of protected lands that make up Shenandoah National Park. There, you can gaze at waterfalls, take in gorgeous sunsets atop rocky peaks, hike sections of the Appalachian Trail, or just cruise The Skyline Drive — the 105-mile road that cuts through the park — with the windows down.

CENTRAL VIRGINIA

From the Vine + Where to Dine

In Central Virginia, many wineries operate as the best kind of one-stop shops, where you can sample amazing wines, indulge in quality cuisine, and even stay the night.

One such venue is Veritas Vineyards, a flourishing family business in the Monticello AVA, with a wine portfolio that runs the gamut from balanced reds to celebration-ready sparkling wines. The tasting room serves up the requisite cheese and charcuterie boards, plus salads, grilled sandwiches, and flavorful flatbreads, while the dining room offers dishes such as shrimp and grits or truffled ravioli, which can be paired with one of the many Veritas varieties available by the glass. After a long day of eating and drinking (or even horseback riding around the property), you can retire to the Veritas Farmhouse with a backdrop of sweeping mountain, field, or vineyard views.

Barboursville Vineyards is another excellent all-in-one option. Come for the award-winning wines, stay for the Palladio Restaurant’s northern Italian-inspired fare, and stay at the 1804 Inn, which features suites in historic cottages.

More great spots include Early Mountain Vineyards (think breathtaking Blue Ridge views and a full restaurant with a seasonal menu revolving around local produce); Stinson Vineyards (featuring wines with a distinct French influence and a rustic inn complete with swimming pool); Pippin Hill Farm & Vineyards (a focus on the marriage of food and wine via vineyard-to-table cuisine featuring ingredients sourced from 10 farm partners); and Ankida Ridge (which wins major points for its remote-though-accessible location, panoramic views, and — thanks to grazing sheep — major pastoral vibes).

What to Do

Head into downtown Charlottesville, just minutes from wine country, and visit The Wool Factory or grab a drink on Quirk’s rooftop.

At The Wool Factory indulge your senses at this distinctive food and beverage destination, located in a historic landmark. After The Wool Factory, Quirk’s rooftop provides the ideal backdrop to celebrating a day in Virginia wine country. The playful cocktails and curated wine list offers something for everyone. Quirk’s vibe is casual yet energetic, perfect for looking forward to the days ahead.

Like your next trip back to Virginia Wine Country, of course.

This article is sponsored by Virginia Wine.