How to Spend a Day Around Middleburg’s Wine Country

The rolling stretch of Route 50 between Aldie and Middleburg—dotted with old stone cottages and fields of grazing horses—gets you to three very good wineries.

Photograph courtesy of Greenhill Winery & Vineyards.

Start at: Chrysalis Vineyards

Chrysalis was popular even before opening a new tasting room in 2015, with walls of windows and big wrap-around decks. Try the Norton, one of its stars. Beyond wine, estate-raised beef is often for sale, and on-site cheesemaking is planned. Tasting: $15.

Next stop: Cana Vineyards and Winery of Middleburg

A few miles down Route 50 is a grand-scale winery that can handle crowds. The adults-only upstairs includes a gazebo, large deck, and TV room. Downstairs are shaded patios and choice spots for picnicking by the vines, with live music every weekend. Try Le Mariage, Cana’s flagship wine, a Bordeaux-style blend anchored by Petit Verdot. Tasting: $10.

Rest stop: Middleburg

Stretch your legs with a walk in downtown Middleburg, the heart of horse country. The National Sporting Library & Museum (102 The Plains Rd.; 540-687-6542; admission $10) exhibits equestrian art, while Middleburg Tack Exchange (103 W. Federal St.; 540-687-6608) sells saddles and riding gear. Tastings of a different sort occur at Mt. Defiance Cidery & Distillery (207 W. Washington St.; 540-687-8100). Middleburg Common Grounds (114 W. Washington St.; 540-687-7065) is a casual spot with all-day breakfast and lunch, including half-smokes with jalapeño mustard and tuna with Tuscan white beans and olives.

Last stop: Greenhill Winery & Vineyards

End the day at one of the rare local vineyards to offer sparkling wine. You can enjoy a glass of Blanc de Blanc on the winery’s lawn, which looks out over forest and mountains. Tasting: $14.

Round trip from DC: 90 miles

Read more from our winery guide: 

This article appears in the May 2017 issue of Washingtonian.

Nancy Bauer

Nancy Bauer is founder of the popular Facebook group, Virginia Wine Love, and the website