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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

  • Road Trip Gift Card

    Road Trip Gift Card

    $80.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • BEST SELLER
    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
  • BEST SELLER
    A person standing at the entrance of a lush garden pathway, looking towards the light at the end of the tunnel created by the archway.

    Whimsical Wonders

    $65 CAD
    Escape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
    • Kid-Friendly
    • Accessible
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area
  • CAN BE DONE IN WINTER
    Black and white photo of an old house.

    An Unusual Adventure

    $50 CAD 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
    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
  • BEST DONE SPRING-FALL
    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
    Can depart from: New York City Area, Trenton Area, Newark Area, Philadelphia Area
  • 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

    $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
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA 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!