Parent and child opening a Guess Where Trips booklet on a picnic bench

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.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • 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
    Red barn with trees behind it.

    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 so much more.
    • Accessible
    • Kid-Friendly
    Can depart from: Boston Area, Springfield, MA Area, Providence Area, Hartford Area
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $65 CAD
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Can depart from: New Haven Area, Hartford Area, Providence Area, Springfield, MA Area