Virginia’s Northern Neck (NNK) National Heritage Area has a lot to offer guests looking for a quiet, relaxing getaway. Less than 2 hours from Washington, DC, Richmond, and Norfolk, the NNK is bursting with history, nature, waterways, art, antiques, quaint small towns, charming inns, delicious restaurants and wineries. It’s the perfect place to Sip & Stay by the Bay this Fall!
1. Chesapeake Bay Wine Country
The Northern Neck George Washington Birthplace AVA (American Viticultural Area) is home to seven members of the Chesapeake Bay Wine Trail (including one cidery, Ditchley Cider Works). Find unique wines, such as Albariño from Ingleside Vineyards and Jacey Vineyards, as well as Petit Manseng from Monroe Bay Winery and Rivah Vineyards at the Grove, which also offers rare Cayuga White.
One of only three places in the world where wine grapes grow on the land next to the waters where oysters are dredged, members of the Chesapeake Bay Wine Trail are located “where the terroir of the grape meets the merroir of the oyster”, a phrase coined by Dudley Patteson, owner of Trail member The Dog and Oyster. What grows together goes together, making the NNK one of the best places on the planet for oyster and wine pairings.
2. Oyster Lover’s Paradise
Virginia is considered the Oyster Capital of the East Coast, thanks to the quality, abundance, and variety of oysters locally harvested. The Northern Neck waters where oysters grow are a unique salinity—highly brackish—giving NNK oysters a distinct light, creamy, and buttery
taste with a clean, crisp finish. Several wineries incorporate oysters and other local seafood into their food and wine offerings. The Colonnade, a fine dining restaurant at Hope & Glory Inn, where The Dog and Oyster is located, serves oysters year round and has crafted many of its wines to complement the bivalves. Ingleside Winery offers the Chesapeake Series Sampler collection, celebrating the lifestyle and heritage of the Chesapeake Bay region. If oysters aren’t your thing, several wineries have onsite kitchen facilities and/or host food trucks on weekends.
3. Special Events
Capitalizing on the legendary oyster trade in the NNK, a number of special events are held celebrating the famous mollusks. The Chesapeake Bay Wine Trail hosts two annual Oyster Crawls: one in the spring and the other in fall. This year’s Fall Oyster Crawl is scheduled for Saturday and Sunday, November 14 & 15. During the event, Good Luck Cellars typically hosts The Tidewater Oyster Gardeners Association, which teaches oyster aquaculture methods, the benefits of growing oysters and, most importantly, awareness of the importance of helping to improve the ecology of the Chesapeake Bay.
Every Sunday, grab brunch at Ditchley Cider Works and sangria at Good Luck Cellars. Entertainment, including musical acts, dance lessons, etc. is provided most weekends at select wineries. Harvest season is a special time at the wineries, with some offering the opportunity to volunteer picking grapes in exchange for wine. Other events in the Northern Neck include The Stratford Hall Wine & Oyster Festival and Irvington Crab Festival, both held in September; and Taste by the Bay, held in November.
4. Discounts
For most events on the Chesapeake Bay Wine Trail, a Tasting Pass can be used to attend. New this year, is a mobile pass being offered in conjunction with Virginia Wine. Each mobile Tasting Pass is good for $5 off your first tasting at each of the Chesapeake Bay Wine Trail’s seven members. Visit all member wineries and be entered to win a private Chesapeake Bay boat cruise for yourself and up to five guests
The Tasting Pass expires July 1, 2027. For more information and to sign up, scroll through Virginia Wine’s Experiences until you come to the Chesapeake Bay Wine Trail Tasting Pass.
5. Quaint Small Towns
Bask in the sun at Virginia’s second longest sand beach, in the Town of Colonial Beach, located in the upper portion of the Northern Neck. Nearby you’ll find Trail wineries Ingleside Vineyards, one of Virginia’s oldest, and Monroe Bay Winery, owned by a French-trained winemaker.
History abounds in and around Montross, located in the middle of the Northern Neck peninsula. Stop at the Westmoreland County Museum & Visitor’s Center, the primary gateway to history and heritage in the Northern Neck. Swing by Trail winery Rivah Vineyards at the Grove for spectacular views of the Yeocomico River, giant yard games, outdoor relaxation. Further south on the peninsula, consider a stop in Kilmarnock, the commercial hub of the NNK, where you’ll find an array of shopping, dining, and Trail members Good Luck Cellars and Ditchley Cider Works. For a quieter, waterfront experience, visit Irvington, home to Trail winery The Dog and Oyster.
6. Lodging on the Chesapeake Bay Wine Trail
Lodging in the Northern Neck ranges from rustic campsites and cabins to luxurious inns and vacation rentals. Guests of the Chesapeake Bay Wine Trail can stay onsite at select locations, including the Manor House at Ditchley Cider Works; the award-winning Hope & Glory Inn, which offers rooms in the inn or private cottages at The Dog and Oyster; and the Cabernet Cottage tiny container house or Airstream at Monroe Bay Winery. Several Trail wineries are members of Harvest Host, offering campsites for tent camping and RV parking. Resort lodging is available at The Tides Inn. Riverview Inn offers a fun, retro feel with modern amenities. Belle Grove Plantation Bed and Breakfast sits on former president James Madison’s birthplace. Other options include the historic Inn at Montross and Kilmarnock Inn. Vacation rentals are also widely available in the region.
7. History
The Northern Neck is called the birthplace of our nation because three of the first five U.S. presidents were born there, including George Washington. Guests can visit George Washington Birthplace National Monument, as well as James Monroe Birthplace; Stratford Hall, the immersive the historic home of the Lee family; and the museum and ruins at Menokin, home of Francis Lightfoot Lee, a signer of the Declaration of Independence. The Steamboat Era Museum preserves and celebrates the steamboats that served as the primary economic and social lifeline for the isolated peninsula before paved roads and bridges existed.
8. Waterways
The Northern Neck peninsula is bounded by the Chesapeake Bay, Potomac River, Rappahannock River, and tributaries providing ample opportunities for watersports, including boating, fishing, swimming, kayaking, paddle boarding, and more. Trail winery Jacey Vineyards is one of the few wineries in the country accessible by boat. Located in a private cove on Mill Creek, just off of the Chesapeake Bay, boaters have docks and plenty of swing room to anchor out deeper draft boats.
9. Nature
Vineyards and wineries are breathtakingly beautiful, especially when autumn’s fall foliage is bursting with colors of red, gold, and orange. Take a stroll through lush vines, which may still hold plump grapes; tall, majestic trees; sunlit waterfronts; small towns decorated for the season; historic buildings; gardens blooming with cool-weather flora; and more. Hughlett Point Natural Area Preserve, in Kilmarnock, offers 1.8 miles of easy dirt, gravel, and sand trails with a woodland boardwalk that leads out to secluded Chesapeake Bay beaches. Westmoreland State Park, in Montross, features cliffside trails overlooking the Potomac River, including paths down to Fossil Beach where you can search for prehistoric shark teeth. Caledon State Park, in King George, is a National Natural Landmark known for its old growth forest and summer home to many American bald eagles.
10. October is Virginia Wine Month
During Virginia Wine Month, wineries in the commonwealth celebrate with special events, seasonal cuisine and pairings, and deals on wine. Here, on the Chesapeake Bay Wine Trail, guests can experience life as a winemaker by joining Good Luck Cellars in harvesting grapes. 
Volunteers who participate in this unique experience learn more about the hand-picked process, have fun and get paid in “good luck” (wine!)
October is also prime cider season, when apples are at peak freshness. Ditchley Cider Works offers a variety of ciders, as well as farm-to-table meat and poultry products. Weekly Sunday Brunch features cider mimosa, cider doughnuts and other seasonal treats.
Start planning your autumn vacation or staycation now in Virginia’s Northern Neck National Heritage Area. Visit the Itineraries page on the Chesapeake Bay Wine Trail website to find more attractions, transportation information, and additional lodging on or near Trail member
sites.