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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Hudson River Hideaways
$65 USDAn iconic road trip route with a twist. Along the Hudson, you’ll uncover hidden hideaways like crumbling ruins, quiet riverside towns, atmospheric cemeteries, and plenty of scenic surprises along the way- Dog-Friendly
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Vibrant Vistas & Picturesque Towns
$65 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
$65 USDIt’s no wonder authors flocked to this part of Massachusetts for inspiration. Set out on a scenic drive through storybook landscapes to discover farms, boardwalk trails, quirky history, and plenty of charming surprises along the way.- Accessible
- Kid-Friendly
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Coastal Connection
SaleRegular price $39.00 USDUnit price perFrom 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
