We like the sound of a little history and a few wineries for a well-rounded Virginia vacation. Discover the history of Virginia as the birthplace of American wine and see how you can experience a perfect pairing of wine and history just about anywhere in the Commonwealth.  

Williamsburg Winery

The Williamsburg Winery
Photo Credit: Kelly J. Mihalcoe LLC

Williamsburg Winery is one of the few wineries in coastal Virginia and is uniquely situated inside Virginia’s Historic Triangle. Just minutes north of Jamestown, the site of the first permanent English settlement in North America, Williamsburg Winery sits on the same land where colonists attempted winemaking nearly 400 years ago. Although the colonists were unsuccessful in producing great vino, the winery harvests a signature Acte 12 Chardonnay made of 100% Virginia grapes as a tribute to its unique history. 

Don’t Miss: Tasting the Acte 12 Chardonnay, named for a 1619 House of Burgesses law which required Virginia landowners to plant 10 grapevines in the name of King James.

Smoke on the Water, Swine & Wine at Upper Shirley Vineyards

Upper Shirley Vineyards

Photo Credit: Creative Dog Media @creativedogmedia
For Wine Lovers

Continue your Virginia Wine adventure at nearby wineries between Williamsburg and Richmond. Upper Shirley Vineyards neighbors Shirley Plantation and offers breathtaking views of the James River from its beautiful low country style setting.

For History Lovers

Discover America's beginnings at the sites of the Historic Triangle. Travel between Jamestown, Yorktown, and Williamsburg along the scenic Colonial Parkway and stop at five historic attractions. 

Where to Stay

Wedmore Place at Williamsburg Winery offers unique, European-inspired rooms. Other great options in nearby Colonial Williamsburg include quaint Colonial Houses, the comfortable Williamsburg Lodge, and the luxurious Williamsburg Inn.

Where to Eat

Enjoy farm-to-table fare at the Gabriel Archer Tavern, located on-site at Williamsburg Winery. The restaurant features a two-level deck overlooking the vineyards, and often hosts live music on warm evening. Other unique dining experiences include the period-appropriate King's Arms Tavern in Colonial Williamsburg and local staple Fat Canary.

Barboursville Vineyards

Barboursville Vineyards
Photo Credit: Hannah Armstrong @hannahelizarmstrong

Virginia entered the modern era of winemaking when Barboursville Vineyards opened in 1976, having successfully planted and established the European vinifera vine on Virginia soil. The vineyard is located near Thomas Jefferson's Monticello, where the founding father attempted and failed to plant the same vines over two centuries ago.

Owner Gianni Zonin, the head of one of Italy’s oldest wine families, set out fulfill Jefferson's dream by making fine wine in Virginia. He found great success and has since set the standard for a region now populated with more than 300 wineries.

Don’t Miss: A tasting of Octagon, Barboursville’s signature Bordeaux blend representing the highest expression of the estate’s European derivation and inspiration.

The exterior of Monticello surrounded by folliage, with the reflection of the home showing in a nearby pool

Monticello

For Wine Lovers

Explore the Monticello Wine Trail, with over 30 wineries scattered throughout Virginia’s bucolic countryside with picturesque views of the Blue Ridge Mountains.

  • Gabriele Rausse Winery: Taste wines crafted by the “Father of Virginia Wine” himself, Gabriele Rausse, the pioneering winemaker at Barboursville Vineyards. 
  • Horton Vineyards: One of Virginia’s oldest wineries, Horton is an industry pioneer for introducing varietal grapes that thrive in Virginia’s climate. Viognier was first planted by owner Dennis Horton and is now widely considered the state grape of Virginia. 
  • Keswick Vineyards: This vineyard sits on the land of two important historical events, one during the Revolutionary War and the other during the Civil War. Include a walking vineyard tour with the winemaker himself!
For History Lovers

Take a Monticello Gardens and Grounds Tour to discover more about Jefferson's interest in botany and explore his home, learning about the free and enslaved people who lived there. Walk the grounds of the University of Virginia, including the Lawn and Academical Village designed by Jefferson. 

Where to Stay

The 1804 Inn and Cottages at Barboursville Vineyards offer well-appointed suites with views of the vineyard and the Blue Ridge Mountains. Nearby accommodations include The Doyle Hotel or The Oakhurst Inn in the heart of Charlottesville.

Where to Eat

Barboursville’s Palladio offers an elegant gastronomic experience including locally sourced Virginia fare through a Northern Italian perspective. For more recommendations, check out our Charlottesville dining guide

Philip Carter Winery

Philip Carter Winery of Virginia
Photo Credit: Bill Crabtree Jr.

The Carter family name carries a 250-year legacy as producers of the first internationally recognized wines in America. Charles Carter, son of the infamous Robert “King” Carter, began growing grapes at his Cleve Plantation in King George County in the 18th century. In 1762, he sent a dozen bottles to England and was awarded a gold medal by the London Society for being the first to make a “spirited attempt towards the accomplishment of their views, respecting wine in America.”

Today, Philip Carter Strother carries on his family’s winemaking legacy as owner of Philip Carter Winery in Fauquier County.

Don’t Miss: A tasting of 2015 Oatlands Norton in the Cleve Hall tasting room or a special educational experience of Wine History in Virginia including a full tasting and pairing with Virginia cheese.

Salamander Resort

Salamander Middleburg

Photo Credit: Sam Dean @sdeanphotos
For Wine Lovers

Choose from several wineries in Fauquier County including:

  • Lost Mountain Vineyards: Bordeaux grapes planted on a rocky Virginia hillside are making Jefferson’s dream a reality, producing world-class wines that marry the elegance of Bordeaux with the bold spirit of California. (Formerly RdV) 
  • Boxwood Estate Winery: This Middleburg winery crafts beautifully blended Bordeaux-style wines and sits on one of the earliest established farms in Virginia.
  • Morais Vineyards & Winery: Morais brings their own family history of winemaking and heritage to Virginia by offering Portuguese-inspired wines in an equally inspired setting.
For History Lovers

Explore a 200-year-old gristmill in Aldie Mill Historic Park. Visit Oatlands Historic House and Gardens, a stately mansion with over 200 years of American history and culture. 

Where to Stay

Stay at the Salamander Resort & Spa in Middleburg for a luxurious experience in the heart of Virginia’s horse country and foothills of the Blue Ridge Mountains. Airlie, set on 300 acres of verdant Virginia landscape, offers warm and welcoming accommodations with plenty of activities and its own fascinating history.

Where to Eat

Farm-to-table fare is a tradition in this area of Virginia. One of America’s finest restaurants is the Inn at Little Washington. More locally-sourced options include Field and Main Restaurant in Marshall and Harrimans Grill at the Salamander Resort. 

Want more local wine? Check out our guide to Virginia wineries, which includes recommendations for wine country, tours, and accommodations.