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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  • BEST SELLER
    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
  • GREAT YEAR-ROUND TRIP
    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 SELLER
    Red barn with trees behind it.

    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 so much more.
    • Accessible
    • Kid-Friendly
    Can depart from: Boston Area, Springfield, MA Area, Providence Area, Hartford Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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