Woman holding four Guess Where Trips envelopes while on road trip

Massachusetts

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • NEW ENGLAND CHARM
    A picturesque street in a New England town with a two-story house adorned with an American flag, surrounded by cozy buildings and greenery.

    Vintage Vibes & Views

    $65 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
  • BEST SELLER
    A winding road surrounded by trees with autumn leaves

    Scenic Sights & Tasty Bites

    $65 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
  • BEST SELLER
    Red barn in a snowy landscape with bare trees.

    Funky Farms & Storybook Tales

    $65 CAD
    It’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
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 CAD
    This 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
  • Last chance!
    A thematic setup featuring items related to witchcraft and Halloween, including pumpkins, candles, books, and various decorative elements on a table.

    Witchy Wonders

    $50 CAD Sale
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

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