Woman holding four Guess Where Trips envelopes while on road trip

Best Day Trips in Delaware

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

Get ready to uncover Delaware’s best-kept secrets on a surprise road trip packed with unique stops and local flavor. Explore charming riverside towns, cross historic covered bridges, and treat yourself to fresh finds at quaint bakeries. Along the way, dive into eerie folklore and tales from the past, all while soaking up the state’s picturesque landscapes. Whether you're a history buff or just looking for a fun adventure, Delaware’s day trips offer a perfect blend of excitement and discovery!

Browse all trips

  • BEST SELLING GIFT
    River running through forest.

    Along the River

    $65 CAD
    Meander through tiny towns along the river that are brimming with hidden gems. There are countless photo-worthy moments and memories to make on this easygoing scenic road trip.
    • Accessible
    • Kid-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Allentown, PA Area, Newark Area, Wilmington, DE Area, New York City Area
  • CAN BE DONE IN WINTER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    If you're the paranormal podcast listener in your friend group, this trip is for you! This area is filled with all things unusual, spooky, and abandoned. You'll also learn about some local legends, ghost stories and folklore throughout your day.
    • Dog-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • COZY WINTER ROAD TRIP
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 CAD
    This trip feels like stepping back in time! Wind your way along quiet country roads to picturesque covered bridges, locally owned bakeries, farmers' markets, and charming small-town shops.
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Wilmington, DE Area
  • PENNSYLVANIA & NEW JERSEY
    Festive Farms & Holiday Charm

    Festive Farms & Holiday Charm

    $65.00 $39.00 CAD
    Celebrate the season with farm-fresh bites, twinkly markets, and festive small-town charm. From history-rich stops to holiday treats and cozy sips, this merry adventure will soon become your new favorite winter tradition.
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: Philadelphia Area, New York Area, New Jersey Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!