For visitors who want a story you can't get anywhere else, these wineries each stake out something singular.
Updated July 2026
Our take: Rankings are our editorial opinion from research and reviews — not paid placements. Policies and hours change, so confirm before visiting.
The ranking
Chrysalis Vineyards at The Ag District
Founded by a Norton champion, it holds the largest single planting of Virginia's native grape in the world, plus an on-site creamery and bakehouse.
Notaviva Farm Brewery & Winery
A music-themed farm winery and brewery where every wine and estate-hop beer is paired to a musical genre.
Tranquility Farm & Winery
The former Otium Cellars pours German and Austrian varietals like Gruner Veltliner and Blaufrankisch on a Hanoverian horse farm.
Boxwood Estate Winery
One hundred percent estate Bordeaux-style wines, a Derenoncourt consultancy, and an architect-designed underground barrel cave.
Breaux Vineyards
Louisiana Cajun heritage, down to the crawfish logo, meets a pioneering Virginia Nebbiolo program.
Hillsborough Winery, Brewery & Vineyard
A historic Fairfax-owned fieldstone estate that runs a winery and a brewery under one roof.
Willowcroft Farm Vineyards
Loudoun County's original winery, open since 1984 in an 1870s barn on the Catoctin Ridge.
October One Vineyard
A downtown wine shop pouring 100% estate-grown wines from a private Bluemont vineyard alongside a curated rotation of other small Virginia producers.
Keep exploring
Browse our ranked best-of lists or line up a safe, chauffeured way to tour the county.