Charlottesville Wine & Food Trail

The Charlottesville Wine and Food Trail links four to five of the Charlottesville, Virginia area's premier wineries and artisan food producers along a scenic driving route through the foothills of the Blue Ridge Mountains. The trail is anchored by properties affiliated with the Monticello Wine Trail, an organization that has promoted the region's wine country since 1989 and represents more than 40 Virginia wineries within Albemarle County and neighboring localities. A typical full-day itinerary begins at Keswick Vineyards on Keswick Winery Drive east of Charlottesville and works westward through estates such as Barboursville Vineyards — one of the oldest in Virginia, founded in 1976 — and King Family Vineyards, known for its Sunday polo matches and Meritage blends. Each stop combines formal wine tastings with local accompaniments: artisan cheeses sourced from Virginia creameries, house-made charcuterie, and small seasonal bites that reflect the agricultural character of central Virginia's Piedmont region. Tasting fees per winery range from $15 to $25 and are often waived with a bottle purchase, making the self-drive route customizable to almost any budget within the $120–$180 per-person range. Those who prefer not to drive can hire a chauffeured guide through operators such as Wine Country Tours, which provides licensed vehicles and knowledgeable drivers for the region's properties. The food component of the trail emphasizes Virginia's growing artisan dairy and cured-meat scene, with stops at creameries producing aged goat and cow's-milk cheeses that pair naturally with the region's Viognier, Cabernet Franc, and Petit Verdot bottlings. The trail is best experienced from April through November when vineyard foliage is at its most striking and all properties are fully staffed.