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.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them!
  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    Vintage Vibes & Views

    $39 CAD
    Immerse 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
    Can depart from: Boston Area, Providence Area
  • BEST SELLING GIFT
    Scenic Sights & Tasty Bites

    Scenic Sights & Tasty Bites

    $39 CAD
    Bakeries, 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
    Can depart from: Boston Area, Providence Area
  • BEST SELLER
    Funky Farms & Storybook Tales

    Funky Farms & Storybook Tales

    $39 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 much more.
    • Accessible
    • Kid-Friendly
    Can depart from: Boston Area, Springfield, MA Area, Providence Area, Hartford Area
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