Woman holding four Guess Where Trips envelopes while on road trip

Philadelphia-Area Road Trips

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

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 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
    A scenic road trip near Allentown along the NJ and PA border with small towns and riverside stops.
    • Accessible
    • Kid-Friendly
    Can depart from: Philadelphia Area, Trenton 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

    $65 CAD
    A spooky Southern New Jersey road trip with abandoned spots, local legends, and eerie stops.
    • Dog-Friendly
    Can depart from: Philadelphia Area, Trenton Area, Wilmington, DE Area
  • 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
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area, Allentown, PA Area, Wilmington, DE Area
  • FATHER'S DAY PICK
    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
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!