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.
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Road Trip Gift Card
Regular price $74.00 USDUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire. -
Hudson River Hideaways
$39 USDAn 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
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Vibrant Vistas & Picturesque Towns
$39 USDHit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.- Dog-Friendly
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Funky Farms & Storybook Tales
$39 USDIt'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
