Trail Wineries

Ten premiere members 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.

Map of Virginia Inset
Backporch Vineyard

Backporch Vineyard takes pride in creating an open and welcoming space for visitors, with 20 acres of land.

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(540) 940-3939

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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(540) 413-6454

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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(757) 710-2890

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 and largest wineries in Virginia. Our 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

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

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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

Holiday Sip & Shop – December 11, 2021

Join participating members for a Holiday Sip & Shop on the Wine Trail. Enjoy holiday refreshments and wine/gift specials at participating wineries. Be sure to “Like” our Facebook page for updates.

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

Photo courtesy Stratford Hall