Arm holding mystery road trip envelope in front of trees and boardwalk

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.

  • Select your trip style.

    Select a day trip based on your location, interests, and travel preferences OR take our quiz to help narrow down options.

  • Get your package.

    Choose between receiving a beautifully crafted package in the mail OR a PDF (digital version) of the trip which gets sent right to your inbox.

  • Pack your car.

    Each package includes a ‘Before You Go’ booklet that will give you just enough information without spoiling the surprise destinations on your road trip.