Touring the Trails of Virginia Wine Country

Virginia Wine Map

An up and coming wine destination unlike any other, Virginia’s deep wine history dates back to Jamestown and the settlers who each tended 10 vines. Vintner Thomas Jefferson made it his life mission to produce a successful vineyard and their experimental harvesting now yields the region’s award-winning wines. Last October, the seventh edition of The World Atlas of Wine by Jancis Robinson and Hugh Johnson featured Virginia wines for the first time. Time Magazine’s article on the book even named Virginia the “newest chapter in American wine history” calling Boxwood Estate’s merlot blends “wines that California would have to respect”. With more than 230 wineries spanning the Commonwealth, there is no better way to take in the vino, scenery and historic sites than through the many trails and tours.

The array of routes allow for a fun, educational day experiencing multiple wineries with two or 20 people. Meet the winemakers, visit a part of the countryside you otherwise wouldn’t and most importantly grow in your knowledge of Virginia wines. Here are a number of trails and tours to check out this season, visit for a state-wide list. Cheers!

The Great Skedaddle: Wine on 29
Pearmund Cellars, Vint Hill Craft Winery and Winery at Bull Run make up this wine trail formed along Route 29, the path of The Great Skedaddle, a term used to describe the unorganized retreat of Union troops back to Washington after their unexpected defeat at the first battle of Bull Run in 1861.

The Blue Ride Wine Way
The Blue Ridge Wine Way is recognized as Virginia’s premier wine region featuring five counties in the Northern Virginia region. Wineries include; Gray Ghost Vineyards, LaGrange Winery, Mediterranean Winery, Molon Lave, Narmada Winery, Oasis Winery, Pearmund Cellars, Rappahannock Cellars and Unicorn Winery. This trail is just under an hour drive from D.C.

Northern Neck/Chesapeake Bay Trail
The Chesapeake Bay Wine Trail features nine wineries which include; Oak Crest Winery, Ingleside Vineyards, Belle Mount Vineyards, General’s Ridge Vineyard, Vault Field Vineyards, Athena Vineyard and Winery, Jacey Vineyards, Good Luck Cellars and The Dog and Oyster. April 26 is the 2nd Annual Spring Oyster Crawl on the Wine Trail. Visit for more information.

Loudoun County Wine Trail
The wine trail of Loudoun Country is so large it is broken into five clusters; Loudoun Heights, Waterford, Potomac, Mosby, Harmony and Snickers Gap. Find the complete list of more than 30 wineries at and look for the developing

211 Scenic Vino Trail
The Vino Trail on Route 211 leads to Shenandoah National Park and runs beside the quaint village of Little Washington. Along the way sit five wineries; Unicorn, Magnolia, Gray Ghost, Narmada, Gadino, Little Washington and Quievremont.

Monticello Wine Trail
The wineries on the Monticello Wine Trail were inspired by Thomas Jefferson’s vision of winemaking and claim the birthplace of American wine. This Charlottesville trail holds 30 wineries.

Area Services and Guided Tour Companies

Divine Wine Tours of Virginia;
Fairfax Va.


Dominion Wine Tour;
Catharpin, Va.


Point to Point Limousines;
Catharpin, Va.


Reston Limousines;
Reston Va.


Chariots for Hire;
Sterling, Va.


Boomerang Tours; Washington


Fairfax Limo Wine Tours; Sterling, Va.


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