7 of the Best Wineries on the Chesapeake Bay Wine Trail

You don’t have to travel all the way to Napa Valley to sample the country’s finest wines. In fact, some of the most delicious pinots and cabernets can be found right here on the Chesapeake Bay Wine Trail! With remarkable views, beautiful weather, and world-class wine, it’s hard to imagine a more perfect way to spend an afternoon. Here’s everything you need to know for planning the ultimate trip!

Your Guide to Chesapeake Bay Wine Trail Tours

The Chesapeake Bay Wine Trail features a total of seven wineries in the Northern Neck and Middle Peninsula regions of Virginia. Readers of Virginia Living voted it the best wine trail in Eastern Virginia in 2013, and, more recently, Savor Virginia readers praised it as the No. 2 wine trail in the whole state. Words simply don’t do it justice — you’ll have to come and experience the Chesapeake Bay Wine Trail for yourself! Make sure to stay several days at the Hope and Glory Inn so you can visit all of these incredible wineries:

1. The Dog and Oyster Vineyard

People relaxing at The Dog and Oyster Vineyard, one of the best things to do in Irvington, VA

When it comes to wineries along the Chesapeake Bay Wine Trail, The Dog and Oyster Vineyard should be at the top of your list! Spanning more than six gorgeous acres of Vinifera and French American Hybrid vines, the vineyard produces four grape varieties: Chardonel, Vidal Blanc, Chambourcin, and Merlot. The best part is that it’s all just a short walk or bike ride away from Hope and Glory Inn! 

Stop in for a tasting of medal-winning wines which are all made from 100% estate-grown grapes. While you’re here, pair your wine with delicious oysters and other tasty bites. Cheers!

2. Good Luck Cellars

You may want to spend a whole day at The Dog and Oyster, but if you’d like to continue your tour, head over to Good Luck Cellars. Owners Paul and Kate began pursuing their passion by making wine in their backyard, and now, they tend to a sprawling, 25-acre vineyard in Kilmarnock! Sip your wine in the cozy tasting room or outside on the 3,000-square-foot, covered, wraparound porch. The views are breathtaking!

3. Ingleside Vineyards 

Next is Ingleside Vineyards, a Virginia favorite since 1980. Similar to The Dog and Oyster Vineyard, their wine varieties have won several awards over the years. Choose from more than 20 different wines and select your favorite! In addition to tastings, Ingleside Vineyards offers free tours of the facility. Learn all about the wine-making process while you explore one of Virginia’s oldest wineries! Afterward, take a stroll through the beautiful courtyard or check out the on-site museum and gift shop. 

4. Caret Cellars

While it doesn’t have the same history as Ingleside, Caret Cellars offers a wine tasting experience like no other. Sip your wine among the stainless steel tanks and French oak barrels inside the winery. Or, find a picnic table outside and enjoy spectacular views of the vineyards. 

5. General’s Ridge Vineyard

At General’s Ridge Vineyard, you’ll find 14 varieties of grapes growing in the fields. A list of delicious wines is the result! With multiple tasting rooms and award-winning wine, this is one stop you won’t want to miss. 

6. Jacey Vineyards

Another popular stop on the Wine Trail is Jacey Vineyards. This small, boutique winery offers a large selection of wine, as well as charcuterie boards, pizza, craft beer, and cider. It spans 150 acres of forests, vineyards, and stunning water views. Plus, it’s one of the only wineries in the country that you can visit via boat! While visitors are welcome to drive to Jacey Vineyards, there are also multiple docks conveniently located in their private cove. 

7. Vault Field Vineyards

Another popular destination for wine in the Northern Neck is Vault Field Vineyards. The owners work hard to take care of their vineyards, which is reflected in the taste and quality of their wines. Their list of grape varieties includes Cabernet Sauvignon and Cabernet Franc vines, Merlot, Vidal, Petit Verdot, Syrah, Chardonel, and Chambourcin.

Insider’s Tips Before You Go

If you want to get the most out of your wine tour, make sure you pick up a free Virginia Wine Trail Passport. It includes a brochure and a wine trail map, and you can earn rewards for visiting multiple wineries. Don’t forget to grab a tasting pass, as well. For just $30, you get one free tasting at each of the wineries. That adds up to an incredible value!

Upcoming Events on the Chesapeake Bay Wine Trail

There are so many fun things to do on the Chesapeake Bay, and the Wine Trail organizes some exciting events as well. If you like local oysters, you’ll be happy to know that there are annual oyster festivals in both the spring and fall! You can also check out Holiday Open Houses at the wineries, a Wine & Cherries Weekend, and plenty of wine festivals. Don’t miss out!

Where Is the Best Place to Stay for a Wine Getaway?

The bedroom in Cottage 3 at the Hope and Glory Inn

When it comes to lodging options along the Chesapeake Bay Wine Trail, look no further than the Hope and Glory Inn in Irvington, VA. Our elegant winery resort features picturesque scenery, luxurious accommodations, and top-notch amenities to ensure that your stay is a relaxing one. All of the best wineries, restaurants, and attractions are just minutes away. Plus, The Dog and Oyster Vineyard is a short walk from our eloquently designed rooms. As soon as you open the door and step inside, you’ll realize why our guests come back again and again!

With two premium queen bedrooms and a spacious living room, Cottage 3 would be a wonderful option for your stay. This quaint cottage is complete with luxury linens, a flat-screen TV, comfortable, country furniture, a private bathroom, and more. Sink into your soft bedding or relax on the private garden patio with a glass of fine wine. There’s no better way to experience the Northern Neck! 

Don’t wait to plan your next getaway. Check our availability and book your stay today!