Woman holding four Guess Where Trips envelopes while on road trip

Winchester, VA

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $39 USD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST SELLER
    Tiny Town Tour

    Tiny Town Tour

    $39 USD
    Meander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • GREAT FALL TRIP
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 USD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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