Foodie Day

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).

Picnic table and vineyard rows at golden hour

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  • 1

    868 Estate Vineyards

    Winery dining at the Vintner's Table (fine dining) or the casual Grill at 868 pavilion.

    Hillsboro · Closed Mon–Tue

    Print details: 14001 Harpers Ferry Rd, Hillsboro, VA 20132 (540) 668-7008 Closed Mon–Tue (typical)
  • 2

    Quattro Goomba's

    Sicilian pizza at the winery.

    Aldie · Closed Mon–Tue

    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)

See all limos, party buses & tours

Stay nearby

Base yourself in Purcellville & Hillsboro to keep the morning drive short and the tasting time long.

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All day plans Drink responsibly