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).

Open this route in Google Maps (opens in new tab)
- 1
Dogs indoors, kids free.
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
Kids and dogs welcome on the ground floor; picnics welcome.
Print details: 38600 Little River Turnpike, Middleburg, VA 20117 (703) 348-2458 Closed Tue–Wed (typical) - 3
Finish where the kids can run at the playground.
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
Book this day
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 Leesburg & Lucketts to keep the morning drive short and the tasting time long.
Some links may earn us a commission at no extra cost to you — see our affiliate disclosure.