Family + Dogs Day

Kid- and dog-friendly stops where the whole crew is welcome, ending at a brewery with a playground.

Where to eat on this route: Thaiverse Middleburg in Middleburg (3.6 mi from the midpoint stop).

Country road linking a vineyard, barn, and village

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

  • 1

    Willowcroft

    Dogs indoors, kids free.

    Leesburg · Closed Tue–Thu

    Print details: 38906 Mt. Gilead Rd, Leesburg, VA 20175 (703) 777-8161 Mon 12:00-17:00; Fri 12:00-19:00; Sat 12:00-19:00; Sun 12:00-17:00
  • 2

    Cana Vineyards

    Kids and dogs welcome on the ground floor; picnics welcome.

    Middleburg · Closed Tue–Wed

    Print details: 38600 Little River Turnpike, Middleburg, VA 20117 (703) 348-2458 Closed Tue–Wed (typical)
  • 3

    Wheatland Spring Brewery

    Finish where the kids can run at the playground.

    Waterford · Open Thu–Sun

    Print details: 38506 John Wolford Rd, Waterford, VA 20197 (540) 687-0035 Thu 11:30-20:00; Fri 11:30-21:00; Sat 11:30-20:00; Sun 11:30-19:00

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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)

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Stay nearby

Base yourself in Leesburg & Lucketts to keep the morning drive short and the tasting time long.

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All day plans Drink responsibly