Chestnut Oak Vineyard

Chestnut Oak Vineyard sits along the Monticello Wine Trail near Charlottesville, Virginia. The property offers views of the surrounding mountains and a calm countryside vibe. Visitors come for approachable Virginia wines and an easygoing tasting experience. It feels like a classic trail stop with modern comforts. Guests can choose curated wine flights, enjoy a glass, or share a bottle. Tastings are available inside the tasting room or outdoors where you can take in the scenery. Seating options lend themselves to small groups and relaxed afternoons. It’s a place to linger. If you’re planning a wine day on the Monticello Wine Trail, this is a convenient addition to your route. Check the website for current hours, seasonal releases, and any updates on reservations, outside food, or pet policies. Weather can shift quickly in the mountains, so bring layers and enjoy the views.