Wine has been a part of Virginia history from the very beginning. None other than Captain John Smith recorded observing grapes floating in the water upon his 1607 arrival in Jamestown, and he quickly grasped the grape-growing potential of the region. Thomas Jefferson, the father of American wine, encouraged his newly liberated countrymen to drink wine with meals and selected Virginia wines for the President's table. At the 1889 Paris World's Fair, a Virginia Claret was proclaimed "one of the World's best wines."

So come on and swirl, sip, and savor wines that have earned world-class reputations without the corresponding world-class price tag. The vineyards are a pleasnt country drive away through stunning and romantic vistas. So whether you're of connoisseur of fine wine or just searching out one of the lesser known secrets of Virginia heritage, you'll find a trip through the Southside Virginia Wine Country a pleasant journey.

Wine Touring Hints...

  • It's always a good idea to call before visiting. Many wineries are small, family-owned operations and may be closed for various family-related activities during the time that you are planning to visit.
  • If visiting in a group of eight or more, please call ahead of time to help the winery prepare for your visit and to make sure they can accept groups.
  • Grape cluster highway signs are posted within a ten-mile radius of each winery. Many of these signs now also will tell you how many miles you have left to go.

Tomahawk Mill Vineyard & Winery


  • Contact: Corky and Nancy Medaglia, proprietors
  • Address: 9221 Anderson Mill Road, Chatham, VA 24531
  • Phone: 434-432-1063 (voice), 434-432-2037 (fax)
  • Internet::
  • E-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.
  • Brief Description:

    Tomahawk Mill Vineyard was first planted in 1988. First plantings were Chardonnay and Concord, with Pinot Noir, Johannisburg Riesling, and Cabernet Sauvignon following. The first crush occurred in 1990. In addition to those wines listed above, you may enjoy their Vidal Blanc, Apple, Mead, Cabernet Franc, Tobacco Road Blues wines.

    The vineyard takes its name from a nearby mill retired from service just before to the first planting after 100 years of continuous operation as a water-powered grist and saw mill. Built by a Confederate soldier, the mill is still essentially intact and slowly being restored. Mill enthusiasts will enjoy a tour of this 19th century workhorse, and all will enjoy tasting wines either in the mill or while strolling through the vineyard overlooking the mill pond.

  • Directions from Chatham: Go west on US-57 for 4.5 miles, right on VA-799 (Climax Road) for 3.4 miles, left on VA-649 (Anderson Mill Road) for 3 miles to the winery on the left.
  • Directions from US-40 East (Rocky Mount): Right on VA-799 (Climax Road) for 7.3 miles, right on VA-649 (Anderson Mill Road) for 3 miles to the winery on the left.
  • Approximate travel time from Chatham: 20 minutes

Stonewall Vineyards & Winery

  • Contact: Larry & Sterry Davis, owners; Bart Davis, winemaker.
  • Address: Rt. 2, Box 107A, Concord, VA 24538
  • Phone: 434-993-2185 (voice), 434-993-3975 (fax)
  • E-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.
  • Brief Description:

    Visitors may enjoy their fine wines on the patio, in the gazebo and picnic grove, or around the fireplace in an European-style tasting room. The vineyard and winery is located in historic Appomattox County, halfway between Lynchburg and Appomattox. Featured wines include Brigade, Regiment, Cayuga, Mist, Mirage, Pyment (Mead), and award-winning vinifera wines.

  • Directions from Chatham: Go north on US-29 to VA-24. Turn right and go 7.5 miles (the road which turns into Villageway Drive) to VA-608. At the Concord light, go north 5 miles on Rt. 608, left 100 yd. on Rt. 721, winery is on the left. Follow signs.
  • Approximate travel time from Chatham: 1 hour, 30 minutes

Hickory Hill Vineyard

  • Contact: Roger & Judy Furrow, owners
  • Address: 1722 Hickory Cove Lane, Moneta, VA 24121
  • Phone: 540-296-1393 (voice)
  • Internet:
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  • Brief Description:

    Hickory Hill Vineyards is a small, family owned and operated vineyard located in the Smith Mountain Lake area 15 minutes from the National D-Day Memorial. Located on a former cattle farm, the winery is the 1923 farmhouse renovated so as not to lose any of its original country charm. The former dining room, converted into a cozy tasting room, is decorated with artifacts and memorabilia found during the renovation. A screened porch and shade trees provide a relaxing quiet, country setting for tasting wine and cheese, for a picnic overlooking the vineyard, or just enjoying the simple pleasures in life. Featured wines include Chardonnay, Cabernet Sauvignon, Vidal Blanc, Smith Mountain Lake Red, Smith Mountain Lake White.

  • Directions from Chatham: Go north on US-29 to US-40 in Gretna. Turn left and go 2 miles to Piney Road. Turn right onto Piney, go 0.2 miles and turn left on Sandy Road. Go 2.6 miles and turn left onto Pittsville Road. Continue for 2-1/4 miles and turn right on Ridgeway Road. Go 14.3 miles (the road will turn into Tolers Ferry Road. Turn right on Smith Mountain Lake Parkway and go 0.2 miles. Turn left on White House Road. Continue for 1.5 miles and then turn left on Skyway Lane. Go 0.3 mi to Tuck Road and turn right. Continue for 1.3 miles and turn left on Radford Church Road. After 1.8 miles (the road turns into Alford Church Road), bear left on Hight Point Road. Follow High Point 1.5 miles to the vineyard as the road changes into Hickory Cove Lane.
  • Approximate travel time from Chatham: 1 hour, 45 minutes

Rebec Vineyards

  • Contact: Richard Hanson, owner.
  • Address: 2229 North Amherst Hwy, Amherst. VA 24521.
  • Phone: 804-946-5168 (voice)
  • E-mail:This email address is being protected from spambots. You need JavaScript enabled to view it.
  • Brief Description:

    Commanding an expansive view of the Blue Ridge Mountains, the Rebec Vineyard winery features rich weathered chestnut siding and exposed beams from a 200-year-old tobacco barn on this National Historic Landmark. Featured wines include Chardonnay, Viognier, Landmark White (dry), Riesling, Gewürztraminer.

  • Directions from Chatham: Go north on US-29, taking the US-501/US-29 to get around Lynchburg (the off-ramp is just after the Mall). Staying on US-29, the vineyard is 5 miles north of Amherst.
  • Approximate travel time from Chatham: 1 hour, 45 minutes


The Homeplace Vineyard


Located in Southside Virginia's Pittsylvania County, was
incorporated in 2004 by Joe and Brenda Williams along with their children Renee and husband Billy, Jesse and wife Penny, and Mary and husband Chris.The Homeplace farm has been in our family for four generations, and we are proud of our heritage.  This farm was originally purchased by Joe's grandparents, Archer L. and Lizzie Yeatts, in 1912. Traditionally a tobacco farm, we planted our first grapes, Traminette, in March, 2005.  We added Cabernet Sauvignon, Chambourcin, and Viognier over the next three years respectively. We currently are tending approximately 5,600
vines on just over 9 acres.