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

  • 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
    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
  • GREAT YEAR-ROUND TRIP
    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
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!