14 Best Wineries Near Chesapeake, VA - Virginia Vacation Guide

The Chesapeake, Virginia is an independent city located in the tidewater region of eastern Virginia. Nearby cities include Norfolk, Virginia Beach, Williamsburg, Newport News, and Hampton Roads.

The Chesapeake Bay region of Virginia also encompasses areas further north, including the Northern Neck, Middle Peninsula, and Lower Peninsula.

The Chespapeake tidewater region is very different from the more mountainous wine regions in the north, west, and central Virginia. The tidewater region is characterised by its close proximity to the water, and some of the wineries in the area even feature their own private docks, plus the ability to reach the winery by boat!

There are some incredible wineries in the area and it is a great place for any wine lover! Below are some of my top picks for the best wineries near Chesapeake, VA.

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Where to Stay

Where to Stay in Williamsburg, Virginia:
Hilton Vacation Club The Historic Powhattan Williamsburg
* * *
Where to Stay in Virginia Beach, Virginia:
Hyatt Place Virginia Beach Town Center
* * *
Where to Stay in Norfolk, Virginia:
Glass Light Hotel & Gallery, Autograph Collection

Want to learn about the EASIEST way to visit some of the best wineries in Virginia? Check out my recommendations for The Best Virginia Wine Bus Tours!

A Map of Wineries Near Chesapeake, VA

Chesapeake Bay Wine Trail

You can start your Chesapeake Wine journey by following the Chesapeake Bay Wine Trail! This trail features 10 member wineries that are all located in Virginia’s Chesapeake Bay Wine Region.

The Chesapeake Bay Wine Trail wineries are below. You can find more details on each winery in the next section.

Backporch Vineyard

Location:

16595 Wilmont, Rd, King George, VA 22485

Compared to some of the other Virginia vineyard, Backporch Vineyard is very new. It began in 2019. It features an Amish barn and has weekly live music events.

Notable wines at the winery include Alba, Cabernet Franc, Cabernet Sauvignon, Chambourcin, Chardonel, Chardonnay, Riesling, and Traminette.

Hours:

Fridays: 4 pm – 8 pm

Saturdays: 12 pm – 7 pm

Sundays: 2 pm – 6 pm

Food:

Food trucks are available, plus visitors can bring their own food.

Dogs Allowed?

Yes.

Caret Cellars

Location:

495 Meadow Landing Ln, Caret, VA 22436

Caret Cellars specializes in Italian wines, including Sangiovese and Pinot Grigio. They also have seasonal special events, including Spring and Fall Oyster Crawls and Wine and Chocolate Pairing.

Hours:

Friday to Sunday: 12 pm – 6 pm

Food:

Light fare is available for purchase. Visitors can also bring their own food.

Dogs Allowed?

Yes.

Ditchley Cider Works & Farm

Location:

1571 Ditchley Rd, Kilmarnock, VA 22482

Ditchley Cider Works and Farm is actually a cidery, featuring hard cider. It also has a lot of history: it is a historic Lee family house featuring a Manor House that dates back to 1752.

The Cidery is great for water views. There is a private beach at the cidery, and visitors can take paddleboarding and kayaking tours. You can also arrive on your own boat. They also offer cooking classes by appointment, as well as a chance to be a “farm hand for a day.”

Hours:

Saturday: 1 pm – 5 pm (Saturdays on the Lawn)
Sunday: 10 am – 3 pm (Sunday Brunch)

Food:

Small plates are available for purchase.

Dogs Allowed?

Yes on the grounds, but not inside.

General’s Ridge Vineyard

Location:

1618 Weldons Dr, Hague, VA 22469

General’s Ridge Vineyard sits on over 100 acres of farmland in Virginia’s Northern Neck. It features a lot of history, with an 1800s farmhouse that has been restored. There is also a two bedroom cottage called Vineyard Views. The vineyard also hosts weddings and other special events at the Carriage House.

Hours:

Friday: 12 pm – 7 pm
Saturday: 12 pm – 6 pm
Sunday: 12 pm – 5 pm

Food:

Light fare is available for purchase, or visitors can bring their own food.

Dogs Allowed?

Yes, in the large tasting room and on the patio.

Good Luck Cellars

Location:

1025 Goodluck Rd, Kilmarnock, VA 22482

Good Luck Cellars is located in the Northern Neck region, and it has 12 rescue dogs on site!

Hours:

Friday and Saturday: 11 am – 6 pm
Sunday: 12 pm – 5 pm

Food:

There are specialty food vendors on select days. They have flavored peanuts, meat/cheese snack packs, and blocks of cheese with crackers for sale. Visitors can also bring their own food.

Dogs Allowed?

Yes, on the porch.

Ingleside Vineyards

Location:

5872 Leedstown Rd, Oak Grove, VA 22443

Ingleside Vineyards is one of the premier Virginia wineries. It has 50 acres of vineyards and has won numerous awards in state, national, and international competitions. They also feature two guest cottages where guests can stay overnight.

They have a large number of special events, including a Summer Music Series, Run the Vineyards 5k, Paint n Sip, and Spring and Fall Oyster Crawls.

Hours:

Monday to Thursday: 12 pm -5 pm
Friday to Sunday: 12 pm – 6 pm

Food:

Cheeses and sausages are available for sale. Visitors can also bring their own food.

Dogs Allowed?

Yes, in the outdoor courtyard and grounds.

Jacey Vineyards

Location:

619 Train Ln, Heathsville, VA 22473

Jacey Vineyards has some unique water features: it has three docks, and it is one of the only vineyards where guests can arrive by boat!

Hours:

Friday: 4 pm -9 pm (Open Mic Night!)
Saturday: 12 pm – 5 pm

Food:

They have charcuterie tapas plates and pizzas for sale.

Dogs Allowed?

Call ahead for more information.

Monroe Bay Winery

Location:

4786 James Monroe Hwy, Colonial Beach, VA 22443

Monroe Bay Winery is a small farm winery and cidery. It features a unique tasting room: it is a strawbale barn made of stained glass wine bottle walls.

Hours:

Friday: check Monroe Bay website
Saturday: 12 pm – 5 pm
Sunday: 12 pm – 5 pm

Food:

Food trucks are sometimes onsite. Visitors can also bring their own food.

Dogs Allowed?

Yes.

Rivah Vineyards at the Grove

Location:

671 Kinsale Bridge Rd, Kinsale, VA 22488

The vineyard is located on the Yeocomico River and has 125 acres of land.

Hours:

May through October:

Friday and Saturday: 1 pm – 8 pm

Sunday: 12 pm – 5 pm

November through April:

Friday – Sunday: 12 pm – 5 pm

Food:

Call ahead for more information.

Dogs Allowed?

Yes, on the grounds only.

The Dog and Oyster

Location:

Irvington, VA 22480

The Dog and Oyster is now known as The Dog and Oyster Micro-Vineyard and Oyster Bar. It also features the Hope and Glory Inn guest accommodations.

Hours:

Saturday: 11 am – 5 pm

Sunday: 12 pm – 5 pm

Food:

They have house-made charcuterie and Bloody Mary oyster shooters.

Dogs Allowed?

Yes.

Additional Chesapeake Wineries

Williamsburg Winery

Location:

5800 Wessex Hundred, Williamsburg, VA 23185

The Williamsburg Winery is conveniently located near Colonial Williamsburg. It is one of my personal favorite wineries to visit in the area. It has a nice outdoor patio area with two levels. There is often live music too, plus a restaurant on site, which makes it a great food destination as well.

The Williamsburg Winery even features Wedmore Place, where guests can stay overnight in one of 28 unique European-styled rooms.

The winery is also a great venue for weddings and other special events.

Hours:

Sunday to Thursday: 12 pm – 5:30 pm

Friday: 12 pm – 6:30 pm

Saturday: 11 am – 6:30 pm

Food:

The winery features some amazing food and inventive dishes at the Gabriel Archer Tavern, which serves brunch, lunch, and dinner. The menu is French-inspired and specializes in farm-to-table dishes such as Summer Street Corn Gnocchi, Spiked Watermelon Gazpacho, and Virginia Ham Benedict.

Dogs Allowed?

Leashed dogs are welcome on the terrace.

Mermaid Winery

Location:

The Mermaid Winery has two locations, in Norfolk and Virginia Beach.

Norfolk Location:

330 W 22nd St, Norfolk, VA 23517

Virginia Beach Location:

4401 Shore Drive, Virginia Beach, VA 23455

Mermaid Winery is another excellent Virginia winery, and it has the added bonus of two locations, one in Norfolk and the other in Virginia Beach, which makes it a great option if you’re in either of those areas.

The winery also hosts many special events, including weddings, bridal showers, and corporate events.

Hours:

Closed Monday

Tuesday to Thursday: 12 pm – 9 pm

Friday and Saturday: 12 pm – 10 pm

Sunday: 12 pm – 9 pm

Food:

The wineries have a substantial menu, including happy hour appetizers such as tacos and spinach artichoke dip, as well as flatbreads, Chicken Pasta, Blackened Tuna, and Shrimp and Grits.

Dogs Allowed?

Call ahead for more information.

Virginia Beach Winery

Location:

1064 Lynnhaven Pkwy #110, Virginia Beach, VA 23452

Virginia Beach Winery features very affordable $5 wine tastings, plus you can get a free tasting when you purchase a bottle or more!

Their wines have colorful names, such as the Tropical Cyclone, Revolutionary Raspberry, and Son of a Peach. The winery also has a selection of olive oils and balsamic vinegars.

They also host regular events, such as a Dance & Wine night and Paint Night.

Hours:

Sunday to Thursday: 12 pm – 5 pm

Friday: 12 pm – 6 pm

Saturday: 12 pm – 6 pm

Food:

Call ahead for more information.

Dogs Allowed?

Call ahead for more information.

New Kent Winery & Talleysville Brewing Company

Location:

8400 Old Church Rd, New Kent, VA 23124

New Kent Winery and Talleysville Brewing Company give visitors the opportunity to try both wine tasting and beer tastings. It is a little further north of the Chesapeake region, but it is well worth the trip.

They feature a substantial selection of both wines and beers. Their wine collection includes Meritage, White Norton (more common among Virginia wines), and Reserve Chardonnay. They have an extensive selection of craft beer, including Pilsner, Lager, Stout, and IPA.