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

    $80.00 USD
    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
    Winter landscape with a river and snow-covered trees under an overcast sky.

    Hudson River Hideaways

    $65 USD
    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 USD
    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 USD
    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
  • Last chance!
    Mother and child walking on a winding road surrounded by greenery

    Enchanted Adventures

    $50 USD Sale
    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?

Take Our Quiz to Find Out

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

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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!