Day Trips in Connecticut

Connecticut is a treasure trove of surprise day trips, offering everything from serene countryside escapes to vibrant urban adventures. The state's compact size means you can easily hop from outdoor fun to cultural exploration and relaxation, all in one day. Discover local gems and hidden treasures as you embrace the spontaneity of a Connecticut road trip. Whether you’re wandering through charming towns or soaking up nature’s beauty, every winding road promises a new experience.

  • 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.
  • 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 SELLER
    Funky Farms & Storybook Tales

    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
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