History + Wine Day

Pair historic estates and manor houses with the wine, from an 1762 manor to an architect-designed cave.

Where to eat on this route: Thaiverse Middleburg in Middleburg (1.6 mi from the midpoint stop).

Picnic table and vineyard rows at golden hour

Open this route in Google Maps (opens in new tab)

  • 1

    Oatlands Historic House

    Begin at the historic house and grounds.

  • 2

    Greenhill Winery

    Tastings at a 1762 manor.

    Middleburg · Open daily

    Print details: 23595 Winery Lane, Middleburg, VA 20117 (540) 687-6968 Open daily (typical)
  • 3

    Boxwood Estate

    Architect-designed cave; 21+.

    Middleburg · Closed Mon–Tue

    Print details: 2042 Burrland Lane, Middleburg, VA 20117 (540) 687-8778 Closed Mon–Tue (typical)

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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 Middleburg & Aldie to keep the morning drive short and the tasting time long.

Browse where to stay

All Loudoun lodging

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All day plans Drink responsibly