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

  • Can be done in winter
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including; crumbling ruins, quaint towns, spooky cemeteries and more.
    • 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
  • 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, colourful 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?

Take Our Quiz to Find Out

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

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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!