A food-forward crawl from a winery restaurant to Sicilian pizza to an upscale Middleburg dinner.
Where to eat on this route: Market in The Gap in Hillsboro (2.4 mi from the midpoint stop).

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- 1
Winery dining at the Vintner's Table (fine dining) or the casual Grill at 868 pavilion.
- 2
Sicilian pizza at the winery.
Print details: 22860 James Monroe Highway (US-15), Aldie, VA 20105 (703) 327-6052 Wed 11:00-20:00; Thu 11:00-20:00; Fri 11:00-20:00; Sat 11:00-20:00; Sun 11:00-18:00 - 3
Middleburg (dinner)
Dinner in Middleburg at Red Fox Inn or Salamander's Harriman's.
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Getting there
A chauffeured tour or designated driver is the safe way to run this route — rural roads, spotty rideshare.
Find a driver or wine tour — Reston Limousine (opens in new tab)
Stay nearby
Base yourself in Purcellville & Hillsboro to keep the morning drive short and the tasting time long.
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