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

A Massachusetts Cranberry Bog Driving Tour

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

New England's First Scenic Drive: Mount Greylock and the Mohawk Trail

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

Berkshires Driving Tours

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

Franklin County Driving Tour

Deerfield River, Shelburne Falls Massachusetts


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 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

Jacob's Ladder Trail

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

Western Massachusetts Foliage Drive

Photo of a river lined with trees with yellow leaves

TripSavvy / Violet Smirnov

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

Classic Cape Cod Driving Tour

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

Massachusetts Fall Foliage and Scenic Drives

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

Massachusetts Foliage Driving Tour

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.