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Check out our blog, “Trail Talk,” for travel tips, recent news, wine pairing suggestions, local history and much more!

Trail Wineries

Nine premier members located in Virginia’s Chesapeake Bay wine region, which encompasses the Northern Neck and Middle Peninsula of Virginia.

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Map of Virginia Inset
Caret Cellars

Caret Cellars is a place where locals and tourists can meet, drink wine and relax in a friendly environment.

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Ditchley Cider Works & Farm

Ditchley is a waterfront 1752 Lee family working farm with cidery, tasting room & B&B. Our ciders and meats/products are sold onsite & online.

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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

We offer estate-grown, hand-crafted wines in Virginia’s historic Northern Neck. Feel free to join us on the porch and enjoy a bottle of our wine while admiring the expansive view of the vineyard and our Grape Vine Patrol Squad.

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Ingleside Vineyards

One of the oldest wineries in Virginia. The European-style courtyard is 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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Monroe Bay Winery

Monroe Bay Winery is a waterfront property near the town of Colonial Beach on part of the James Monroe Birthplace Farm land.

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(804) 410-5628

Rivah Vineyards at the Grove

Rivah Vineyards at the Grove offers 125 scenic acres of farm, woods and riverfront on the Yeocomico River.

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The Dog and Oyster

Enjoy the one-of-a-kind culinary experience of pairing Coastal Virginia oysters and wine within a micro-vineyard and within a town Coastal Living named one of their “Top Ten”.

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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

Fall Oyster Crawl – Nov. 9 & 10, 2024

Join participating trail members for one of our most popular events, the Fall Oyster Crawl. Find out why Virginia is for Lovers… of Wine and Oysters! Be sure to “Like” our Facebook page and sign up on our email list (see below) for updates.

Our Trail members also host their own events frequently throughout the year. Please visit individual member websites and follow us on social media for updates.

Photo courtesy Stratford Hall