The 3 Best Vineyard/Wineries Around Winchester

Virginia’s wine scene is blooming, with nearly 300 wineries spread across its rolling hills and vineyards that date back to the 17th century. Today, the Shenandoah Valley AVA shines as one of the state’s premier regions, offering varietals that range from crisp Chardonnay to bold Cabernet Franc. By acreage and grape production, Virginia ranks fifth in the nation, a testament to both its heritage vines and its modern winemakers’ grape expectations.

Valerie Hill Vineyard & Winery

At Valerie Hill, history and hospitality go hand in hand. Set around a Federal-style brick home dating to 1807, this family-owned farm winery pours estate-grown vintages that reflect over two centuries of local terroir. Visitors can sample award-winning reds and whites inside the charming farmhouse or on the shaded lawn—lite fare available—while imagining the generations who first tended these vines.

Briedé Family Vineyards

Briedé Family Vineyards offers a French-style boutique experience just minutes from downtown Winchester. Paul and Loretta Briede craft small-batch wines from unique varietals like Marquette, Pinot Meunier and La Crescent, all grown sustainably on their 25-acre estate. Live music twice weekly pairs perfectly with imported French cheeses, and their medal haul—from the Shenandoah Cup to the Atlantic Seaboard Competition—proves that these pours aren’t horsing around.

James Charles Winery & Vineyard

Every sip at James Charles Winery tells a story of craft and community. With 97 Wine Enthusiast awards of 85 points or higher, their winemaker’s dedication shines in both robust reds and bright whites. The pet- and family-friendly patio hosts live music and seasonal events, making it easy to vine and dine beneath the Shenandoah sky. Their wine club enrollment reads like a wish list of tasting privileges and member-only discounts, ensuring that loyal fans never run out of reasons to raise a glass.

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