The pull of the past has brought tourists to central Virginia for years, what with Monticello, Thomas Jefferson’s famous abode, smack in the heart of the region. But today more and more oenophiles are turning their attention to Albemarle County, home of the Monticello American Viticultural Area. With forty wineries along what’s marketed as the Monticello Wine Trail, visitors can partake of multiple afternoons of tastings in the vicinity. Here’s where to find superlative sips.

For award-winning vintages: Barboursville

Barboursville Vineyards was the first Virginia winery to enjoy commercial success, and it’s the gold standard for Commonwealth juice today. The estate was founded forty-seven years ago by two Italian viticulturists who brought a European vision to the region. Go for the best in class Octagon vintage, then stay for dinner at the exceptional on-site restaurant, Palladio.
For a romantic horse ride through the vines: Veritas

One of the most unique ways to experience Virginia wine is on horseback, and with Indian Summer Guide Service, you can take to the saddle through the scenic vineyards of Veritas before heading to the tasting room for exceptional pairings from lead winemaker Emily Hodson.
For bucolic views: Jefferson Vineyards
Jefferson Vineyards sits just below Monticello and happens to include a portion of land on which the founding father first attempted to grow grapes nearly 250 years ago. To further strengthen the historic tie, in March the Thomas Jefferson Foundation purchased the winery. For a full day exploring the past, visit Monticello, then head down the “little mountain” to find a picnic spot on the vineyard’s great lawn as you share a bottle of the property’s petit manseng.
For a great girlfriend gathering place: Pippin Hill Farm & Vineyards

There’s something about its dramatic vantage point overlooking the Blue Ridge Mountains that makes Pippin Hill catnip to rosé-loving bachelorette parties. Even more enticing are the many group-friendly activities the vineyard hosts, including cooking classes and watercolor painting tutorials.
For wine with a side of polo: King Family Vineyards

If Charlottesville feels empty on a Sunday, you can bet it’s polo day at King Family Vineyards. The vast estate has its own polo field and team, and each summer Sunday through October (weather permitting), the perimeter of the field becomes a tailgate party for its polo matches. Cheer on the home team with a bottle of the winery’s signature Crosé wine.
For putt putt and petit verdot: Keswick Vineyards
As far as picturesque villages go, you won’t find one prettier than the charming hamlet of Keswick. But even vast estate owners like to have a little fun. Just stop by Keswick Vineyards for proof. Its stunning outdoor tasting room often hosts entertainment like karaoke and has its own on-site mini golf course, where visitors are invited to putt and sip. If it’s hot, grab a frosé.