Woman holding four Guess Where Trips envelopes while on road trip

Day Trips in Pennsylvania

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

Set off on a surprise day trip through Pennsylvania’s picturesque landscapes, where enchanting adventures are just around the corner. Wander through charming small towns, cross historic covered bridges, and indulge in treats from local markets. With whimsical gardens, scenic river towns, ghostly tales, and iconic spots like Gettysburg, these day trips are packed with vibrant history, natural beauty, and plenty of surprises.

Browse all trips

  • BEST SELLER
    River running through forest.

    Along the River

    $65 CAD
    A scenic road trip near Allentown along the NJ and PA border with small towns and riverside stops.
    • Accessible
    • Kid-Friendly
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    A spooky Southern New Jersey road trip with abandoned spots, local legends, and eerie stops.
    • Dog-Friendly
  • A PERFECT COUNTRYSIDE DRIVE
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 CAD
    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
  • GREAT SUMMER ROADTRIP
    The Shore Explorer

    The Shore Explorer

    $65 CAD
    Hop from shore to shore on this iconic beachside road trip just a short drive from the tri-state area. Alongside beaches, you'll also explore waterside boardwalks, age-old lighthouses, scenic viewpoints, and delicious local eateries.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • Digital Download Only
    A monument at Gettysburg, featuring a statue on top of a classical Revival dome, surrounded by an open field under a partly cloudy sky.

    Secrets of Gettysburg

    Regular price $39.00 CAD
    Explore Gettysburg and its surrounding area in a whole new way. We’ve made this classic, All-American, bucket list destination easy and fun to do - whether it's your first or fiftieth time! Discover hidden gems and surprising stops while learning more about the turning point of the Civil War.
    • Kid-Friendly
    • Dog-Friendly
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!