9 Best Wine Trails in Virginia

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Did you know that there are over 300 wineries in Virginia and dozens of wine trails that make it easy to explore a particular region of the state while admiring the views and checking out small towns along the way? Virginia is a prime yet underrated destination for wine lovers, but you can learn a lot about wine and have a memorable time while touring the local vineyards and wineries.

To help you plan your route, here are some of the best wine trails in Virginia that feature multiple wine stops in the state.

Virginia Peninsula Wine Trail
Uncork and unwind along the Virginia Peninsula Wine Trail, nestled in an Atlantic Coastal Plain area

Virginia Peninsula Wine Trail

The Virginia Peninsula Wine Trail is situated in an Atlantic Coastal plan and features the following wineries: Gauthier Vineyard, Jolene Family Winery, New Kent Winery, Saudé Creek Vineyards, Upper Shirley Vineyards and Williamsburg Winery. A winery experience here may make you think you’re actually in Europe because of the subtropical maritime climate, fine hospitality, and excellent wines. The wine-growing region here is unique because of the climate and is defined by the York and Pamunkey Rivers to the north and the James River to the south. At the end of the day, you can stay at Wedmore Place, the Williamsburg Winery’s on-site hotel that is reminiscent of a European inn, or the Fife & Drum Inn, which is in a walkable location in the heart of Colonial Williamsburg.

Chesapeake Bay Wine Trail
Good Luck Cellars

Chesapeake Bay Wine Trail

The Chesapeake Bay Wine Trail is made up of the following Virginia wineries: Caret Cellars, The Dog and Oyster Vineyard, General’s Ridge Vineyard, Good Luck Cellars, Ingleside Vineyards, Jacey Vineyards, and Rivah Vineyards at the Grove. The wine region is in the Northern Neck and Middle Peninsula of Virginia. People love visiting this region because of the fresh seafood, American history, lively watersports, and relaxed accommodations. You can take tours and experience tastings at the member wineries, and there is a tasting pass that gives you access to a free tasting at each winery along the trail. There are also some fun events scheduled in the trail area, such as the Spring Oyster Crawl.  

Fauquier County Wine Trail
Boxwood Winery

Fauquier County Wine Trail

The Fauquier Country Wine Trail involves 24 wineries and vineyards, and each one offers its own unique experience in the foothills of the Blue Ridge Mountains. The member wineries include the following: Arterra Winery, Aspen Dale Winery at the Barn, Barrel Oak Winery, Blue Valley Vineyards, Boxwood Winery, Chateau O’Brien Winery, Cobbler Mountain Cellars, Delaplane Cellars, Fox Meadow Winery, Granite Heights Winery, Linden Vineyards, Mediterranean Cellars, Molon Lave Vineyards, Morais Vineyard, Naked Mountain Winery, Pearmund Cellars, Philip Carter Winery, Rogers Ford Winery, Slater Run Vineyards, Three Fox Vineyards, and Vint Hill Craft Winery. The Fauquier County website offers suggestions for places to stay and other things to do as you experience the wineries on this trail.

Foothills Scenic Wine Trail
DuCard Vineyards

Foothills Scenic Wine Trail

There are also very small wine trails worth visiting in Virginia, such as the Foothills Scenic Wine Trail, which has just two small, family-run wineries as members. Sharp Rock Vineyards in Sperryville and DuCard Vineyards in Etlan are two wineries that you don’t want to miss while visiting this part of Virginia. It is less than two hours from Washington and Richmond. There are hiking opportunities nearby, as well as some nice restaurants and inns.

Heart of Virginia Wine Trail
James River Cellars Winery

Heart of Virginia Wine Trail

Five of the premier wineries in central Virginia are part of the Heart of Virginia Wine Trail: Grayhaven Winery, James River Cellars Winery, Lake Anna Winery, Mattaponi Winery, and Fifty-Third Winery & Vineyard. This is a convenient wine trail to check out from nearby Richmond, Charlottesville, and Fredericksburg.  Most of the trail wineries have food available for purchase. There is a HOVA passport ticket that you can buy to get a basic wine flight option at all five wineries, plus a souvenir wine glass.

Monticello Wine Trail
Barboursville Vineyards

Monticello Wine Trail

There are over 40 wineries that are part of the Monticello Wine Trail, and they are split into five regions: Western Trail, Eastern Trail, Southern Trail, Northern Trail, and Gateway North. The wineries here were inspired by Thomas Jefferson’s vision of growing grapes and making wine. It is a historical trail full of Virginia winemaking heritage and is considered to be the birthplace of American wine. All wineries are within 25 miles of Charlottesville. The trail’s website is a good resource for learning about wine trail events, wine week specials, and wine competitions.

Shenandoah Valley Wine Trail
Shenandoah Valley Wine Trail

Shenandoah Valley Wine Trail

Along the Shenandoah Valley Wine Trail, you can experience a unique wine-growing region with higher elevation, limestone soil, less rainfall, and cooler nights than elsewhere in the state. These conditions translate to unique varieties of wine, which pair well with the beauty of the Blue Ridge, Massanutten, and Allegheny Mountains. The Shenandoah Valley Wine Festival takes place each year in June. There are over 20 member wineries and vineyards along the trail.

SoVA Wine Trail
Bright Meadows Farm along the wine trail

SoVA Wine Trail

The SoVA Wine Trail is made up of 12 boutique wineries in southern Virginia. Visitors can pick up a passport book at any participating winery for $20 and get tastings at all of the wineries and a souvenir wine glass. If you get stamps from all of the wineries, you can be entered in a drawing to win a prize. When you are in this part of the state, you can also learn about Civil War history because of the abundance of battlefields nearby.

Nelson 151 Trail
Nelson 151
Valley Road Vineyards in Nelson 151

Nelson 151 Trail

The Nelson 151 trail is unique because it combines wine with other craft beverages, local food, unique lodging, and stunning natural beauty. It is on the Sunrise Side of the Blue Ridge and along a state-designated scenic byway. There’s a little something for everyone who enjoys a good beverage on this trail, including beer, cider, and craft spirits. There are seven wineries, three distilleries, three cideries, and four breweries on this trail. Stay at a charming B&B, roadside inn, or vacation rental home in the mountains at the end of your day and make a full weekend out of your adventure!

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