A low-mileage day anchored in and around Leesburg, from vineyard brunch to downtown breweries to a King Street dinner.
Where to eat on this route: SideBar in Leesburg (0.0 mi from the midpoint stop).

Open this route in Google Maps (opens in new tab)
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Brunch plus views to open the day.
Print details: 19925 Hogback Mountain Road, Leesburg, VA 20175 (703) 777-2797 Closed Tue–Wed (typical) - 2
Walkable downtown Leesburg brewery stop.
Print details: 11 S King St, Leesburg, VA 20175 (571) 707-8014 Mon 15:00-21:00; Tue 15:00-21:00; Wed 15:00-21:00; Thu 15:00-21:00; Fri 12:00-22:00; Sat 12:00-22:00; Sun 12:00-18:00 - 3
Second downtown Leesburg brewery, steps away.
Print details: 205 Harrison St SE, Suite 100, Leesburg, VA 20175 (571) 918-4446 Mon 15:00-22:00; Tue 15:00-22:00; Wed 15:00-22:00; Thu 15:00-22:00; Fri 15:00-23:00; Sat 11:30-23:00; Sun 11:30-19:00 - 4
Cap the tastings at the downtown estate-wine shop before dinner.
Print details: 7 Loudoun St SW, Leesburg, VA 20175 (571) 641-6907 Thu 16:00-20:00; Fri 12:00-20:00; Sat 12:00-20:00; Sun 12:00-18:00 - 5
King Street (dinner)
Wrap up with dinner on downtown Leesburg's King Street.
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.
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