This Small Virginia City Has a One-of-a-kind Wine Scene Served With Southern Hospitality

The vineyards and wineries along Monticello Wine Trail offer tastings for oenophiles, those just discovering their wine palate, and everyone in between.

Vineyards at King Family Vineyards
Photo: Aaron Watson Photography

Charlottesville has long been known for the University of Virginia (the only university in the U.S. to be named a UNESCO World Heritage Site) and Monticello, former president Thomas Jefferson's home. It's also right in the middle of Virginia Wine Country, where more than 40 wineries produce delicious blends, including reds, whites, rosés, and specialty wines, for both wine aficionados and novices to enjoy.

While it's easy to make the comparison to Napa Valley or New York's Finger Lakes region — rolling hills, impressive culinary pedigrees, endless options of where to spend a leisurely day among the vineyards — Charlottesville and its surrounding wineries throughout Albermarle County are special in their own right. There's a relaxed type of Southern hospitality that pairs perfectly with an afternoon of wine flights and outdoor picnics. Not to mention, many of the area's wineries are dog-friendly and few require reservations.

Choosing which wineries along the Monticello Wine Trail to visit can be tough, though — all 40 are within 25 miles of Charlottesville, and each offers guests a sample of local flavors with flights and the occasional tasting menu. Below, we've rounded up some of the most popular and best Charlottesville-area spots to try some crisp, bold, or rich Virginia varieties.

Barboursville Vineyards

Pamper your palate tasting the award-winning wines at Barboursville Vineyards, a winery owned by northern Italians. Then, take in the views of the region's mountains from the lawn, and check out the on-property ruins of the Thomas Jefferson–designed Barbour Mansion. Overnighters can bed down at the property's inn, where restored interiors are a refined mix of damask, oil paintings, four-poster beds, and clawfoot tubs.

Pippin Hill Farm & Vineyards

Wine Tasting at Pippin Hill Farms
Courtesy of Pippin Hill Farms

Expect fresh, seasonal ingredients and boutique wines at Pippin Hill Farm & Vineyards. One of the area's leading wedding venues, Pippin Hill pairs an elevated food pairings menu with an exploration of their wines — chardonnays, sauvignon blancs, and cabernet francs, to name just a few. You'll need to make a reservation for the more in-depth tour and tasting, but wine flights don't require one — and they're best enjoyed overlooking the vineyards and the Blue Ridge Mountains.

Keswick Vineyards

Aerial view of Keswick Vineyards with white house in distance
Courtesy of Keswick Vineyards

Family-run Keswick Vineyards, which opened in 2000, sits 15 minutes from downtown Charlottesville and smack dab in the middle of Virginia Wine Country. There's plenty of outdoor space at the winery, with an alfresco tasting bar and tables open to customers. Light snacks are provided with tastings, but if you want a larger meal, you're welcome to bring a picnic with you to feast on under the courtyard's umbrellas.

King Family Vineyards

Vineyards at King Family Vineyards
Aaron Watson Photography

King Family Vineyards offers several wine tasting options, including self-guided wine tastings of four varieties and an in-person guided tasting of five wines — reservations aren't required. With over 30 acres of vineyards, the team produces whites, reds, and rosés. If you choose to sip in the tasting room, you'll find a stone fireplace as well as a selection of salamis, cheeses, spreads, and some french bread to pair with your wine. Outside, there's a covered veranda, brick patio, and lawn to partake in a wine-fueled lunch.

Veritas Vineyard

Wine Tasting at Veritas Winery near Charlottesville, Virginia
Abby Grace Photography

Guests get the full Virginia winery experience at Veritas Vineyard, a family-owned and -run winery 30 minutes from Downtown Charlottesville. There's ample seating outside on the lawn (bring your own chair or blanket), on the Bricks (where you can feast on a picnic paired with wine from the bar), or in the tasting room (reservations are suggested). Visitors can also choose to spend the night at The Farmhouse at Veritas B&B, a six-room inn with nods to the family's English heritage.

Early Mountain Vineyards

Tasting room house at Early Mountain
Courtesy of Early Mountain

It's not just the wine bringing people to Early Mountain Vineyards; the award-winning tasting room, seasonal produce, and elegant decor appeal help create an unforgettable experience for guests. Pick up a wine flight, a bottle, or just a glass from the walk-up pavilion, and head to the meadow, where you'll find picnic table seating and umbrellas to shade you from the Virginia sun.

Blenheim Vineyards

Blenheim Vineyards at Sunset
Courtesy of Blenheim Vineyards

Blenheim Vineyards is well-known throughout the region, partly due to its famous owner, Dave Matthews, who established the winery in 2000. Make a reservation to experience the indoor tasting room via a seated wine tasting, or find a seat outside, where you can taste the fruits of the Blenheim team's labor by flight, bottle, or glass. Whereas other wineries have larger food selections, at Blenheim, it's all about the reds, whites, and rosés. For those who require snacks and nibble with their grapes, there's the option to bring your own food or pre-order a cheese selection.

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