Massachusetts Fall Foliage Driving Tours

Massachusetts offers a bounty of options for leaf lovers looking to drive and explore. If you've only been to the Berkshires, it's time to branch out and find new regions of Massachusetts that come alive with color starting in September. Here are some Massachusetts fall foliage driving tours to consider as you plan your autumn outings. Remember to follow your instincts, too, and don't pass by beautiful byways that beckon to you.


  • 01 of 09
    Home sitting next to a cranberry bog in carver, Massachusetts


    Ken Wiedemann/Getty Images

    It's a colorful sight to behold when Massachusetts' largest cash crop is harvested each fall, and changing leaves add to the visual splendor. Follow these tips and directions to enjoy your own tour of Cranberry Country: the region south of Boston.

  • 02 of 09
    Country road at Mount Greylock in Massachusetts

    Sarah Kastner/STOCK4B/Getty Images


    This scenic drive through the Berkshires of western Massachusetts is one of 30 scenic drives featured in the book "Backroads of New England." Read this book excerpt, and plan a fall drive to the top of Mount Greylock and along New England's first official scenic road, which is more than a century old.

  • 03 of 09
    Road in Cheshire Massachusetts through the Berkshires

    Thomas H. Mitchell/Getty Images

    From the Mohawk Trail Association, here are five suggested driving tours in western Massachusetts that are perfect for any season, especially fall. 


  • 04 of 09
    Deerfield River, Shelburne Falls Massachusetts


    Posnov/Getty Images

     This tour takes you through classic New England towns including Greenfield, Ashfield, Buckland, Shelburne Falls, South Deerfield and Deerfield. Yankee Candle Village is a must-stop while you're in this part of Massachusetts.

    Continue to 5 of 9 below.
  • 05 of 09
    Church in lee city, berkshire district Massachusetts

    Jose Fuste Raga/Getty Images

    Jacob's Ladder Trail is the colorful nickname for U.S. Route 20 in Massachusetts, a hilly and picturesque alternative to the Mass Pike. The country's first auto road built to climb over a mountain range is also a National Scenic Byway.


  • 06 of 09
    Connecticut river winding throught the Pioneer Valley in Massachusetts


    Denis Tangney Jr./Getty Images

    Trace the Connecticut River on this 60-mile foliage drive, described in Yankee magazine. You'll see old cemeteries, farms, small towns, funky shops and historic sights.

  • 07 of 09
    Photo overlooking cape cod and martha's vineyard

    Thomas H. Mitchell/Getty Images

    From National Geographic, this "drive of a lifetime" takes in practically all of the Cape. Use it to navigate your way to classic Cape Cod scenes if you're visiting in the fall. If you're visiting New England late in the fall foliage season, the Cape is one of the last places where leaves typically hang on each year.


  • 08 of 09
    Small bridge in Plymouth Massachusetts

    Denis Tangney Jr./Getty Images

    Visit New England provides suggested scenic driving routes throughout Massachusetts, including drives in the Berkshires, along the south shore, in the Greater Boston area and more.


    Continue to 9 of 9 below.
  • 09 of 09
    Bridge of Flowers in Shelburne Falls, Massachusetts


    Rick Friedman/Contributor/Getty Images

    From Yankee magazine, explore the hill towns of western Massachusetts on this two-day fall driving tour.

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