The Ashby Inn & Restaurant
This is a deep, red leaning cellar of nearly 600 wines, built around Bordeaux varietal reds and serious Burgundy on both colors, with Champagne well represented through houses like Billecart Salmon and Taittinger. The spine is classic and collector minded: Old World Chardonnay and Pinot Noir run alongside California Cabernet and cult bottles like Bond, and the top of the list climbs into Domaine de la Romanee Conti and Petrus at four and five figures. That said, it stays usable, with a median around $145 and bottles starting at $11, so you can find honest value if you know where to look. Note the Virginia local presence in Linden Vineyards and Boxwood Estate, a good talking point with guests. The 16 wines by the glass are modest against the size of the list, so this is a cellar that rewards drinkers who commit to a bottle.