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Our Guide to Visiting the Monticello Wine Trail

Visiting the Monticello Wine Trail

The Charlottesville, Virginia region is known for its great wines. But with about 40 wineries spread out in different directions all around the city, how to tackle Charlottesville wine country, sometimes also known as the Monticello Wine Trail, depends on how much time you’re spending there.

While we have shared some of our favorite wineries across both Charlottesville and Central Virginia in previous posts, this is our guide to visiting the Monticello Wine Trail, an active association of wineries, all within 25 miles of Charlottesville, Virginia. We can personally attest to these places and their wines, as these are some of our favorite wineries to stop by when we’re in the area. But I admit this is a representative sample; we couldn’t list every single winery. If we didn’t mention one, that does not mean that you should avoid it.

Background of Charlottesville, Virginia Wine Country

This wine region is known by many as the birthplace of American wine, as it’s where President Thomas Jefferson first attempted to make wine back in 1807. While his initial efforts failed, others took up the mantle, and the wine region grew, with many winemakers making impressive strides from the 1970s to today. The Monticello American Viticultural Area comprises one-third of Virginia’s vineyard acres and produces some of the best wine in Virginia. Many of these wines have won national and international acclaim.

If You Have Only One Day for Visiting the Monticello Wine Trail: Go South to the Wineries on Carter Mountain

Visiting the Monticello Wine Trail
Gabriele Rausse Winery

Some of the wineries in Charlottesville’s Wine Country are just a few miles south of Charlottesville’s downtown area, on or near Carter Mountain. This mountain is also where you’ll find Monticello, Thomas Jefferson’s historic home, and Highland, President James Monroe’s estate. At some of these wineries you’re sampling wine while surrounded by lush forest.

A few of our favorite wineries in this area include tiny Gabriele Rausse Winery, Michael Shaps Wineworks, Jefferson Vineyards, and Blenheim Vineyards, which is owned by musician Dave Matthews of the Dave Matthews Band.

If You Have a Couple of Days for Visiting the Monticello Wine Trail: Venture Northwest Toward the Blue Ridge Mountains

Visiting the Monticello Wine Trail

About 30 minutes northwest of Charlottesville is a cluster of wineries at the foot of the Blue Ridge, where you can enjoy stunning views of the hills.

Some of our go-to wineries in this part of Charlottesville Wine Country include exotic-looking Glass House Winery, King Family Vineyards, Pollak Vineyards, and Stinson Vineyards (look out for the chickens).

If You Have One More Day: Go Northeast to Orange County

The towns of Gordonsville and Barboursville in Orange County, around 30 minutes northeast of Charlottesville, are home to several wineries. We tend to visit these wineries on our way to or from Charlottesville. The wineries in this region include the well-known Barboursville Vineyards, as well as Reynard Florence Winery and Honeh Lee Vineyard.

Visiting the Monticello Wine Trail
Barboursville Vineyards

If You Can Squeeze it in: Go Further West to the Nelson 151 Route

A little further west of Charlottesville, closer to the Blue Ridge Mountains and the Appalachian Trail, are several wineries, cideries, distilleries, and breweries along Route 151 in Nelson County, which calls itself “Virginia’s Long Weekend Address.”

When we’re on this part of the Monticello Wine Trail some of our favorite places are Afton Mountain Vineyards (the lake is particularly pretty), Veritas Vineyards and Winery, and the smaller Flying Fox Vineyard and Winery.

Visiting the Monticello Wine Trail
Afton Mountain Winery

While not officially a part of the Monticello Wine Trail, the region also hosts a number of other interesting places to grab a drink. To switch it up, we recommend Bold Rock Nellysford Cidery, featuring a variety of dry, sweet, and seasonal ciders, as well as Blue Mountain Brewery, with an ever-changing menu of beers and an option to try a flight of 10 (that’s not a typo!)

We hope our guide to visiting the Monticello Wine Trail will be helpful as you plan your next trip to the region. Please let us know if you have suggestions on what other wineries we should add to this list. Our email is

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