11. Middleburg, VA
Why go: About an hour west of Washington D.C., the quaint town of Middleburg is at the heart of hunt country. But throughout Loudoun and Fauquier Counties, next to the polo fields and equestrian eventing facilities throughout the region, you’ll find 44 wineries—like Barrel Oak Winery, Boxwood Winery, Greenhill Winery, and Cana Vineyards—within 198 square miles producing chardonnays, bordeaux varietals, and more.
Where to stay: The historic Goodstone Inn & Restaurant dates back to 1768, but was converted from an estate to an inn in 1998. Now, it offers seasonal dishes with ingredients pulled straight from the Inn’s farm. There are miles of nature trails throughout its 265-acre property. It makes for a luxurious home base for winery hopping.
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