This Scenic 33-Mile Drive Just May Be The Most Underrated Adventure In Massachusetts

If you’re looking for a truly unique Massachusetts adventure that doesn’t take much more planning than filling up your gas tank, you should definitely check out Jacob’s Ladder Scenic Byway. This rural roadway winds through the Berkshire foothills and will take you into beautiful forests, along breathtaking rivers, and through charming small towns.

Western Massachusetts Scenic Byways

Jacob’s Ladder Scenic Byway is part of Route 20. The scenic route lasts about 33 miles and is a great way to experience the untouched splendor of some of Massachusetts’ most picturesque parks and villages.

Google/Brian Stec

This scenic byway offers miles of hiking and skiing just off the road. Head to Chester-Blandford State Forest to explore two of the area’s most beautiful waterfalls, Sanderson Brook and Goldmine Brook.

October Mountain State Forest in Lee is actually Massachusetts’ largest state forest, with over 16,500 acres of wilderness to discover. If you want a more catered experience, head to Canterbury Farms in Beckett for 12 miles of groomed trails with equipment rentals available.

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Google/John Duffy

Feel like hitting the water? This byway will take you by the gorgeous Westfield River, where you can try your hand at whitewater rapids. If you want a tamer experience, head to the Housatonic River for a gentle float through fields, forests, and floodplains. Look for boat launches in Lenox and Lenox Dale.

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Flickr/Andrew Wertz

Of course, this byway isn’t just about natural beauty. The road will also take you through the towns of Chester, Russell, and Huntington, where you’ll find everything from a restored 1840s railroad station to classic New England church spires.

Flickr/C Hanchey

History lovers should stop off in Lee Center, where you’ll find plenty of beautiful 19th-century architecture and family-run shops selling everything from homemade bread to locally designed fashion.

Google/Jacob's Pillow Dance

Music lovers can’t miss a stop in Lenox, just off the byway. There you’ll find Tanglewood, the summer home of the Boston Symphony Orchestra and plenty of talented guest musicians. If you’re driving through in the summer, try to time your visit with one of their outdoor concerts and enjoy a picnic on the grass. If art is your thing, don’t forget to head to the Jacob’s Pillow Dance Festival in Becket for performances from more than 50 internationally recognized dance companies during this summer celebration.

Whether you want to experience pristine natural beauty, charming and historic villages, or just an afternoon of wandering, the Jacob’s Ladder Scenic Byway is a great option. Click here to find out more about the route and where to hop on near you. For another great road trip, check out this drive that will take you to some of the state’s best waterfalls.