Day Trips in Massachusetts
Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.
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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Vintage Vibes & Views
$39 USDImmerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and picturesque beaches.- Kid-Friendly
- Dog-Friendly
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Scenic Sights & Tasty Bites
$65 USDBakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the ideal trip for your whole road trip crew. The perfect road trip for any Little Women movie fans, too!- Accessible
- Kid-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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Escape to the Cape
$65 USDThis road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.- Kid-Friendly
- Dog-Friendly
