Woman holding four Guess Where Trips envelopes while on road trip

Connecticut

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

  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • Can be done in winter
    Hudson River Hideaways

    Hudson River Hideaways

    $65 USD
    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 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
  • Can be done in winter
    Woman in winter looking up at snow flakes

    Funky Farms & Storybook Tales

    $65 USD
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and much more.
    • Accessible
    • Kid-Friendly
    Can depart from: Boston Area, Springfield, MA Area, Providence Area, Hartford Area
  • explore beach towns
    Boardwalk leading to a beach.

    Coastal Connection

    $65 USD
    Feel the ocean breeze in your hair as you go from beaches and boardwalks to independent shops and eateries. There are a few unusual surprises in this trip that will keep you on your toes! This is a great trip to do from the New Haven and Hartford area.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Can depart from: New Haven Area, Hartford Area, Providence Area, Springfield, MA 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!