Take a (Road, Boat or Plane) Trip to the Chesapeake Bay Wine Trail

CBWT map

It’s that time of year when we roll down the windows, open the sunroofs, put the tops down, and take to the road, sea and air, cruising to the sounds of our favorite tunes. A visit to the Chesapeake Bay Wine Trail is a fun trip, whether your preferred mode of transportation is auto, boat or plane.

LOCATION, LOCATION, LOCATION

Water at Rivah Vineyards
Water at Rivah Vineyards

Most of the members of The Chesapeake Bay Wine Trail are located in the Northern Neck (NNK) of Virginia, with one winery just over the bridge on the Middle Peninsula. The Northern Neck is the northernmost of three peninsulas on the western shore of the Chesapeake Bay; the Middle Peninsula is, obviously, the middle peninsula, accessible from the NNK by the Norris Bridge.

The Northern Neck’s northern border begins in King George County, Virginia, fewer than 60 land miles from Washington, DC. In this region of the NNK, you’ll find Trail wineries Ingleside Vineyards, in Oak Grove, and Monroe Bay Winery, in Colonial Beach, on the Potomac River, about 35 nautical miles from the Chesapeake Bay.

In the middle region of the Northern Neck, about 25 land miles southeast, is General’s Ridge Vineyard, in Hague; Rivah Vineyards at the Grove, in Kinsale, on the Yeocomico River; and Caret Cellars, located just over the Rappahannock River, in Caret.

Dockside table at Ditchley
Dockside table at Ditchley

Thirty land miles further and you’ll arrive at the southern region of the NNK, sandwiched between the Chesapeake Bay and Rappahannock River, about 50 land miles from Newport News, 70 from Richmond. This area of the Northern Neck is home to Jacey Vineyards, in Heathsville; Ditchley Cider Works and Good Luck Cellars, in Kilmarnock; and The Dog and Oyster in Irvington.

GETTING HERE BY LAND, AIR, SEA… EVEN HORSEBACK!

Bounded by the Chesapeake Bay and the Potomac and Rappahannock Rivers, the Northern Neck is easily accessible by sea, as well as land. Several Trail wineries are located directly on the water, some with boat access and their own docks.

Boating dock at Ditchley
Boating dock at Ditchley

Access Ditchley Cider Works’ protected, deep water cove from the Chesapeake Bay via Dividing Creek. Drop anchor at the cidery’s 100-ft. dock and spend the day sipping cider, lounging on the modest sandy beach or paddle boarding and kayaking in the private cove.

Dock at Jacey Vineyards
Dock at Jacey Vineyards

Seven docks are in Jacey Vineyards’ private Corbin Cove, off of Mill Creek, in Northumberland County, and accessible from the Chesapeake Bay. A commercial dock is under construction near the mouth of the creek. Further, a marina is located just down the road.

Located just across Monroe Bay from Colonial Beach, waterfront Monroe Bay Winery is accessible by road, boat, trolley and plane! The local trolley transports guests to/from various points in town, including the winery. Seaplanes are regularly observed landing in Monroe Bay, which is only a short rideshare to another Trail winery, Ingleside Vineyards.

Small aircraft landing at Caret Cellars
Small aircraft landing at Caret Cellars

At Caret Cellars, light aircraft have landed right on the vineyard’s grounds; and horses and buggies are not unheard of at Rivah Vineyards at the Grove!

Horse and buggy at Rivah Vineyards
Horse and buggy at Rivah Vineyards

Drop anchor at a nearby marina and commission a rideshare for the short drives to General’s Ridge Vineyard, Good Luck Cellars, and The Dog and Oyster, the latter of which has a private boat for hotel guests, True Love.

STAY ON THE TRAIL: From Camp Sites to Luxury Lodging

Did you know you can stay overnight on the Chesapeake Bay Wine Trail? Several Trail members have accommodations, ranging from rustic to luxurious.

Ditchley Manor House
Manor House at Ditchley

Situated on a 160-acre working farm, the historic 1752 Manor House at Ditchley Cider Works & Farm has four bedrooms and sleeps up to eight. Rental of the house includes full breakfast for up to eight guests each morning, seven stand up paddleboards (SUPs), WiFi and 40 AMP EV charger. Guests are invited to “be a farmer for a day” and tend to cattle, hogs, ducks, geese and turkeys; learn about strawbale gardening; and pick vegetables. Ditchley also features Sunday Brunch weekly.

The Dog and Oyster is located on the grounds of the award-winning Hope & Glory Inn. The boutique inn boasts six guest rooms in the historic bed and breakfast, opened in 1889 as a schoolhouse. Historical references remain, with common areas including “Detention”, the full service bar; “Hooky”, an outdoor dining area; and “The Colonnade” fine dining restaurant, named for the 10 Doric columns that frame the space. In addition, seven quaint cottages dot the “secret garden” on the property, complete with manicured grounds, garden sculptures, a saltwater pool, and a romantic, open-air garden bath. Each one- and two-story cottage is uniquely decorated in luxurious, shabby-chic décor and haute couture designs.

Manor house at General's Ridge
Manor house at General’s Ridge

Watch the sun rise and gaze out over the vineyards from the large wraparound porch and balcony at General’s Ridge Vineyard’s mid-1800s Manor House. Three bedrooms, two bathrooms, a full kitchen, dining room, bar and several sitting rooms sleep six comfortably. A second option is Vineyard Views, a  two-bedroom cottage hidden among the grapevines. The cottage also includes a full kitchen, dining room, sitting rooms and a deck, on the  almost one hundred acre property.

Container house at Monroe Bay Winery
Container house at Monroe Bay Winery

Cabernet Cottage, the tiny container house at Monroe Bay Winery, blends 160 sq. ft. of indoor  luxury living space with the natural beauty of the farmland to create a harmonious connection. Measuring 8 ft. x 20 ft., the container features a large door at one end and a screened French Door on one side. Inside is a well-appointed kitchenette, full bathroom, and sofa/day bed that serves as a couch and pull-out bed for two people. Adirondack chairs on the porch offer views of the farmland, with winery’s Straw Bale Barn Tasting Room and waterfront just a short stroll away. A kayak is available for guest use.

Bring your RV! Caret Cellars and Rivah Vineyards at the Grove are members of Harvest Hosts, offering limited space for unique RV camping.

OFFSITE LODGING

Along the Chesapeake Bay Wine Trail route are quaint small towns and rural villages, many with waterfront and beach accommodations, historic and colonial architecture, world class resorts, charming cottages, rustic cabins, private vacation rentals, boutique inns and natural campsites. Visit our Itineraries page to find lodging close to each of our Trail member sites.

Watch for our next blog post, where we will share fun activities at Trail wineries, cool attractions in the surrounding areas, and more to help you plan your perfect road or boat trip!

Cheers!

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