Leesburg Home-Base Day (no long drives)

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).

Country road linking a vineyard, barn, and village

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

  • 1

    Stone Tower Winery

    Brunch plus views to open the day.

    Leesburg · Closed Tue–Wed

    Print details: 19925 Hogback Mountain Road, Leesburg, VA 20175 (703) 777-2797 Closed Tue–Wed (typical)
  • 2

    Black Hoof Brewing

    Walkable downtown Leesburg brewery stop.

    Leesburg · Open daily

    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

    Crooked Run

    Second downtown Leesburg brewery, steps away.

    Leesburg · Open daily

    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

    October One Vineyard

    Cap the tastings at the downtown estate-wine shop before dinner.

    Leesburg · Open Thu–Sun

    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.

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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