Woman holding four Guess Where Trips envelopes while on road trip

Surprise New York Day Trips

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

Set out from the hustle and bustle of NYC for a road trip full of surprises. Explore charming small towns and lush landscapes just beyond the city, where historic ruins, whimsical gardens, and storybook-like streets are waiting. With scenic trails, vibrant views, and markets that offer a bit of everything, these day trips are the perfect way to uncover a different side of New York.

Browse all trips

  • BEST SELLING TRIP
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist. Along the Hudson, you’ll uncover hidden hideaways like crumbling ruins, quiet riverside towns, atmospheric cemeteries, and plenty of scenic surprises along the way
    • Dog-Friendly
    Can depart from: New York City Area, Newark Area, Hartford Area, New Haven Area
  • CAN BE DONE IN WINTER
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 CAD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
    Can depart from: Hartford Area, New Haven Area, Springfield, MA 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
  • PERFECT FOR FAMILIES
    Enchanted Adventures

    Enchanted Adventures

    $65 CAD
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colorful photo ops and tasty treats.
    • Kid-Friendly
    Can depart from: New York City Area, Philadelphia Area, Trenton Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!