Fall is one of the best times of the year to visit Virginia wineries particularly October, when Virginia Wine Month is celebrated. Despite the absence of large scale events, wineries across the Commonwealth are welcoming wine lovers in search of a pre-holiday getaway. But with many of Virginia’s 300+ wineries entering a new, important phase in top flight service and hospitality, where are some of the best to visit and what can one expect?


Acres of wine grapes at Cave Ridge Vineyard
Cave Ridge Vineyard (credit: Cave Ridge Vineyard, Facebook)


Cave Ridge Vineyard

1476 Conicville Road
Mount Jackson, VA  22842
(540) 477-2585

Current Hours: Sunday to Friday 12 p.m. to 6 p.m., Saturday 12 p.m. to 7 p.m.

A breathtaking property overlooking the Shenandoah Valley, Cave Ridge Vineyard is welcoming its visitors daily for only outdoor seating at this time. While no wine tasting is currently available, Cave Ridge is offering wine flights, along with a nice selection of light food options. Cave Ridge is slated to host a number of upcoming events, including its lavish Harvest Wine Dinner on Saturday, October 10.

Family owned and operated since 2005 by Randy and Karen Phillips, Cave Ridge Vineyard produces a number of exceptional varietal wines across 25 acres. Selections include French choices that the Virginia wine industry is best known for, like Cabernet Franc, Chardonnay, Petit Verdot and Syrah. Additionally, the Phillips, along with their daughter/business manager Megan, also feature award-winning blends like Cuvée Select and Fossil Hill Reserve. In February, Randy Phillips was honored with the Gordon Murchie Lifetime Achievement Award for significant contributions to the Virginia wine industry.


Related: Where To Dine In The Fabulous Northern Virginia Wine Country


Greenhill Winery & Vineyards

23595 Winery Lane
Middleburg, VA  20117
(540) 687-6968

Current Hours: Monday-Thursday, 12 p.m. to 6 p.m., Friday-Sunday, 12 p.m.to 7 p.m.

Founded in 2013 by David Greenhill, Green Hill Winery & Vineyards is among the great wineries of the acclaimed Middleburg AVA in Northern Virginia. Open daily to guests 21 and over, the winery is currently offering a Wine & Food Experience, with selected Virginia wines and cheese/charcuterie. The winery’s main building is open weekdays for limited indoor and patio seating on a first-come, first-serve basis.

On weekends, advance reservations are required but only available for wine club members. Exterior seating requires no reservation, but parties of 10 or more are not allowed. Located just east of the vibrant community of Middleburg, the 128-acre property produces a number of single grape French wines like Cabernet Franc and Petit Manseng, along with superb blends like Superstition.


Related: Where To Stay In Virginia’s Hunt & Wine Country


Jefferson Vineyards

1353 Thomas Jefferson Parkway
Charlottesville, VA  22902
(434) 977-3042

Current Hours: Friday-Thursday from 11 a.m. to 6 p.m.

Of all the many notable Virginia wineries along the Monticello Wine Trail, none has a more prominent place in history than Jefferson Vineyards. It’s not the state’s oldest, but it resides on Thomas Jefferson’s former vineyard property, then known as the Birthplace of American Wine. Reestablished in 1981 by Stanley and Shirley Woodward, the Virginia wine icon produces French varietals and blends across over 20 acres from its 650-acre estate.

Just minutes from James Monroe’s Highland, Michie Tavern and Monticello, Jefferson Vineyards is open to visitors 21 and over. Service is only available outdoors, on a first-come, first-serve basis, with seasonal wine flight and food items like charcuterie and cheeses. Among wine selections available are Cabernet Franc, Petit Verdot and its acclaimed Viognier. Priced slightly higher is the 2017 Jefferson’s Own Estate Reserve, a gold medal winner at this year’s Virginia Governor Cup.


Related: The Clifton: Finest Luxury Boutique In Charlottesville, Virginia


Upper Shirley Vineyards

600 Shirley Plantation Road
Charles City, VA  23030
(804) 829-9463

Current Hours: Dining, Wednesday-Sunday, 11 a.m. to 4 p.m., Wine Service Wednesday-Sunday 11 a.m. to 5 p.m.

Upper Shirley Vineyards is offering food and beverage services at its 14,000 sq. ft. property above the James River. A gourmet Fall Picnic Menu from Chef Carlisle Bannister is available, in addition to wine bottle, glass service and tasting kits. Premium selections include French wines like Merlot, Petit Verdot and Viognier. Seating is available for fine Virginia wine is on a first-come, first-serve basis only in the tasting room and outdoor space. Located about halfway between Richmond and Williamsburg, Upper Shirley Vineyards also features live music on selected dates. Established in 2013, Upper Shirley Vineyards is owned and operated by Tayloe and Suzy Dameron.


Williamsburg Winery

5800 Wessex Hundred
Williamsburg, VA  23185
(757) 229-0999

Current Hours: Sunday – Thursday 12 p.m. to 5 p.m., Saturday-Sunday 12 p.m. to 7 p.m.

Although its tasting room remains closed due to current state mandates, other attractions are open at Williamsburg Winery. This includes the wine shop, outdoor pavilion, casual dining and luxury accommodations. Wine flights and bottles of wine are available for purchase at the 1619 Wine Pavilion. Additionally, Gabriel Archer Tavern is open for dining with limited capacity indoors and outdoors.

Reservations are available for overnight stays at the winery’s 4-star, 28-room Wedmore Place. Encompassing 300 acres, Williamsburg Winery was established in 1985 by Belgium-native Patrick Duffeler and his late wife Peggy. However, it’s located on one of the oldest wine producing properties in Virginia, dating back to the 17th century. Williamsburg Winery holds 50 acres of vineyards, with French varietals like Cabernet Franc, Chardonnay, Petit Verdot and Viognier.


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About The Author:

Randy Yagi is an award-winning freelance writer who served as the National Travel Writer for CBS Local from 2012-2019. More than 900 of his stories still appear in syndication across 23 CBS Local websites, including CBS New York, CBS Los Angeles, CBS Chicago and CBS San Francisco. During his peak years with CBS, he reportedly had a digital audience reach of 489 million and more than 5.5 million monthly visitors. His other stories have also appeared in the Daily Meal, Examiner.com, CBS Radio, Engadget and Radio.com. He is a Media Fellow of Stanford University, U.S. Army veteran and lifelong resident of Santa Cruz County, California.