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 SELLER
    River running through forest.

    Along the River

    $29 USD Sale
    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
    Sale
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Newark Area, Wilmington, DE Area, New York City Area
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $29 USD Sale
    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
    Sale
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • GREAT FALL TRIP
    Red covered bridge over water.

    Covered Bridges & Baked Goods

    $29 USD Sale
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Wilmington, DE Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

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!