The Essential Guide to Charlottesville and Albemarle County’s Monticello Wine Trail

The viticultural renown of wines from old-world countries has defined the standard of winemaking excellence for centuries. In many cases, a bottle of wine from France, Italy, or Spain is assumed to boast an impressive history—with this assumption often accompanied by an equally astounding price tag. 

It was precisely this legacy, quality, and prestige that inspired Thomas Jefferson to explore winemaking from his Albemarle County home in Charlottesville, Virginia. 

Today, eight American Viticulture Areas (AVAs) now reside within the state’s ten winemaking regions—the oldest of which is the Monticello AVA. This winemaking area holds some of the state’s earliest vineyards surrounding the city of Charlottesville. It draws increasing numbers of visitors and winemakers to the foothills of the Blue Ridge Mountains each year.

More than forty wineries along the Monticello Wine Trail within the greater Charlottesville area invite wine amateurs and aficionados alike to taste the region’s history through wine—and to stay a while. Find your own perfect pairing along the Monticello Wine Trail at these top wineries and vineyards.  

Three Stops to Kick off Virginia Wine Month

Eastwood Farm & Winery

Just 5 miles outside of Charlottesville on Carters Mountain Ridge, 77 sprawling acres of apple and pear orchards, publicly accessible hiking trails, and raspberry vines designate Eastwood Farm & Winery, an original estate dating back to the 1800s. Opened in May 2020, this female-owned and family-operated winery produces award-winning wines that were most recently granted multiple silver and gold medals during the 2022 Virginia Governor’s Cup. 

Try the original Tall Tails white blend made from Virginia-grown apples and pears, or the raspberry rosé, featuring berries harvested from the Eastwood estate. With an extensive diversity of additional wine varieties, Eastwood wines are perfect for summer sipping or autumnal unwinding within one of the estate’s three tasting venues. 

Pair small plates from the Eastwood culinary team at the barn and veranda, or snag an adirondack chair beneath the tent and terrace before happy hour at the Eastwood Grill. The rotating menu of food truck bites is perfectly paired with the wines and ciders on tap, with options for the whole family.

Loving Cup Vineyard & Winery 

Celebrating its tenth anniversary as the only certified organic vineyard in Virginia and one of three on the East Coast, Loving Cup Vineyard & Winery is a family-owned winery in the heart of the Monticello AVA. Specializing in hybrid grapes and wines, Loving Cup is currently testing eight new grape varieties well-suited to organic farming and less susceptible to disease. 

The star white grape variety in this vineyard, the cayuga, is a French-American hybrid that truly embodies the history of Virginia wine. The sparkling, rosé, and red blend wines are artfully crafted from all organic fruits, all of which are grown on-site at the foothills of the Blue Ridge Mountains in Albemarle County. 

Visit the vineyard for a tasting from April to December, or roll up your sleeves to join the Loving Cup family for a day of planting, cluster-thinning, and shoot positioning. The fruits of your labor include a 25 percent discount on all Loving Cup wines for one year.

Blenheim Vineyards

While Blenheim Vineyards was founded in 2000, the property upon which its 32 acres of estate vineyards now reside dates back to the early eighteenth century. Assorted structures remain on the property, including a school, chapel, smokehouse, library, and Gothic-Revival-style cottage. They evoke memories of Virginia’s colonial past. The grapes produced today, however, are signals of Virginia’s viticultural future. 

Tree-like fractals and vibrant portraits splashed across each Blenheim bottle are exciting departures from other bottle labels at the grocery store, and the wines inside blended from grapes like grüner veltliner, cabernet franc, and merlot form an extensive varietal profile. Try a glass of the 2020 Painted Red blend in the estate’s tasting room, designed by Blenheim’s owner and founder, Dave Matthews of Dave Matthews Band.

The building, intended to leave minimal environmental impact, requires no electricity during the summer. Guests may reserve guided tasting experiences to sample the available varieties, and to—in the words of Matthews himself—“drink and be merry.”

Check out this complete list of wineries in Charlottesville and Albemarle County, and prepare to celebrate Virginia Wine Month.