Trail Wineries

Eight premiere wineries located in Virginia’s Chesapeake Bay wine region, which encompasses the Northern Neck and Middle Peninsula of Virginia.

Click on the map icons or the list below to view more information.

Caret Cellars

The wine trail’s newest member. Caret Cellars is a place where locals and tourists can meet, drink wine and relax in a friendly environment.

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(540) 413-6454

General’s Ridge Vineyard

This historic 150+ year-old estate has 3 tasting and event rooms, and 2 short term rental homes.

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Good Luck Cellars

Join us for Friday Wine Down, bring your supper and enjoy a bottle of our wine on our porch!

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Ingleside Vineyards

One of the oldest and largest wineries in Virginia, Ingleside features a European-style courtyard, perfect for a glass of wine and picnic lunch.

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Jacey Vineyards

Located on Mill Creek, visit us by boat or car.  Anchor out or stay in a Villa.

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Oak Crest Vineyard & Winery

Come experience the quiet oasis of our small chateau-style winery and friendly staff.

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The Dog and Oyster

Home of the world’s largest corkscrews and the Virginia Wine and Oyster Classic.

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Vault Field Vineyards

Located on historic Vault Field Farm near the town of Kinsale, in the heart of Virginia’s Northern Neck.

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Area Attractions

Activities & Events

Tours & Tastings

Sample award-winning varietals, learn pairing tips, or enjoy tours of winemaking facilities. Bring a picnic and your friends. Days and time vary by winery (view their schedules). Also, check out our limited-edition Tasting Pass to enjoy a free tasting at each winery on the Trail!

Photo courtesy Stephanie Campbell 

Upcoming Events

Spring Oyster Crawl – April 21-22, 2018

Join the wineries of our Trail for our Spring Oyster Crawl. Each participating winery will offer one or more oyster dishes to pair with its wines.  Be sure to “Like” our Facebook page for updates leading up to the event.

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Photo courtesy Stratford Hall