Trail Wineries
Nine premier 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.
Caret Cellars
Caret Cellars is a place where locals and tourists can meet, drink wine and relax in a friendly environment.
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.
804-435-3851
General’s Ridge Vineyard
This historic 150+ year-old estate has 3 tasting and event rooms, and 2 short term rental homes.
804-472-3172
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.
804-435-1416
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.
804-224-8687
Jacey Vineyards
Located on Mill Creek, visit us by boat or car. Anchor out or stay in a Villa.
804-580-4053
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.
(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.
757-621-0618
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”.
804-438-6053
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 22 & 23, 2023
Join participating trail members for our annual Spring Oyster Crawl! Find out why Virginia is for lovers… of wine and oysters! 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