Parent and child opening a Guess Where Trips booklet on a picnic bench

Washington, D.C. & Maryland Day Trips

Ready to escape the hustle and bustle of the capital? The areas around D.C., Maryland, and Virginia are a day-tripper's dream, packed with history, culture, and natural beauty. Explore charming towns, dive into outdoor adventures, or uncover historical gems – all just a short drive from Washington, D.C. Whether you're in the mood for a peaceful retreat or a cultural deep dive, a one-day surprise road trip in the DMV area is the perfect way to mix things up!

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • BEST SELLER
    A large American flag hanging on the side of a red brick building with greenery in the background.

    Tiny Town Tour

    $65 CAD
    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 FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views.
    • Kid-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • DIGITAL ONLY
    Woman spinning on the beach.

    Waterside Bliss

    $39.00 CAD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area
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