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.

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  • Gift Card [Digital $CAD]

    Gift Card [Digital $CAD]

    $74.00 CAD
    Instantly send the gift of a one-day surprise road trip! The gift card covers the full price of one of our mailed trips, including taxes and shipping.
  • 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
  • Can be done in winter
    Woman in winter looking up at snow flakes

    Funky Farms & Storybook Tales

    $65 CAD
    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 CAD
    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

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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!