Virginia Route 20 is one of the alternative routes to Charlottesville - do yourself a big favor and bail off U.S. 29 in Ruckersville if you drive down to Charlottesville any time of the year (particularly the fall). The highway north of C'Ville resembles Route 7 in Tysons Corner on a bad day. You'll want to stop at 7-11 and grab a bottle of Glen Ellen to survive that highway, thus ruining a great Virginia wine experience that awaits you.
The Route 20 Wine Route starts in Barboursville and ends in Scottsville, which is about 20 miles south of Charlottesville. A few wine destinations (some famous; others not so famous) are must-stops--including Barboursville, of course. There is a small town (more of a crossroads) named Barboursville, but this name is famous for its vineyard and winery, one of Virginia's originals (planted in 1976). If the Smithsonian operated a winery, it would probably resemble Barboursville. There is a restaurant (Palladio) on the premises as well. Rows of visitors descend on the tasting bar every weekend, no matter what season. World renowned for its Octagon red blend, Barboursville wines can be found in supermarkets all of the state (as well as the occasional Sunoco station) - this is a mass producing winery. There is something for everyone here, and the prices are right. The drawback of a place this large is the lack of space for "unwineding." On warm days, you can bring your own picnic and enjoy a bottle or three near the fascinating Barboursville Ruins. Photo ops at nearly every turn.
Driving a few miles south on Route 20, make a right turn off and follow the signs to Burnley Vineyards. Not as well-known as Barboursville (or Horton, which lies east of route 20 on the road towards yet another "ville"-- Gordonsville), Burnley is one year younger than Barboursville; first vines planted in 1977. Most likely, you will be greeted by the owners with a glass of warm mulled wine in hand. The tasting room is the polar opposite of Barboursville's slickness and the room in the back, for unwineding, is a mishmash of tables with folding chairs and old rolling office chairs. Highly unusual, and that describes the wines too. They are probably the only Virginia winery that offers a Red Zinfandel (grapes trucked in from California). A guest house if offered for those who want to wrap up the first half of the Route 20 jaunt.
As route 20 approaches Charlottesville, you can see the quaint city tucked into the foothills to the west. Continue on route 20 south and follow the signs to Jefferson Vineyards, the closest winery to Monticello. Another pioneer of the Virginia wine scene, Jefferson Vineyards is perched up on a hillside and offers a terrific Riesling (semi dry).
After the detour to Jefferson Vineyards (and Monticello for a glimpse of Gabriele Rausse's vineyard on TJ's estate grounds), return to route 20 southbound, and follow the signs to Sugarleaf Vineyards. The Long and Winding Road - a song appropriate for the gravel road leading to Sugarleaf (second after the road leading to Stone Mountain for "winery offroading" in Virginia). Sadly the former winemaker at Sugarleaf, Dan Neumeister, passed away a few years ago in a fatal motorcycle accident. His favorite tree on the Sugarleaf property, which also adorns the labels of their wines, greets visitors to this unique boutique location.
Continue on 20 south, and take a left turn before crossing the bridge and visit the Commonwealth's "celebrity wineries" (which exist side by side): Trump Vineyard (which opened in late 2011, on the property that used to be Kluge Estate Vineyards) and Blenheim Vineyards (owned by Dave Matthews). The experiences at these wineries fit the personalities of their owners to a tee--overdone, expensive, and elite for Trump Vineyard; Earth-friendly, unpretentious and naturally beautiful for Blenheim.
The final two wineries on the Route 20 Trail are next to each other as well: First Colony Winery and Virginia Wineworks. First Colony is one of the blogmasters' favorites in the state - every wine's a winner. The tasting room is more traditional, versus the "working winery" atmosphere of Virginia Wineworks, which is over the hill and through the woods, about half a mile from First Colony. Michael Shaps, the winemaker at Virginia Wineworks, is one of the Godfathers of Virginia wine, and the wines under his name are among the best on the east coast. The more affordable label, Virginia Wineworks, contains incredibly priced outstanding wines (including wine a box....the first Virginia winery to offer this.) According to the tasting room hostess, a picnic area is coming for the warmer months.
One trail, nine wineries, which, typical for Virginia, are completely different from each other. After Virginia Wineworks, find a place for an overnight (a tent will do at this point) and prepare for the next jaunt - the Virginia Route 6 Wine Trail......
First Colony Winery