Why take the Mass Turnpike when you can take a scenic route, at least for a little while, instead? Running alongside the Turnpike for much of its 35 miles, Route 20, also known as Jacob’s Ladder Trail, provides a scenic alternative to highway travel. If you haven’t heard of this scenic back road in Massachusetts before, you will certainly want to take it the next time you find yourself in the Berkshires. So come along with us as we traverse the spectacular Jacob’s Ladder Scenic Byway!

The Jacob's Ladder Trail Scenic Byway is a 35-mile portion of U.S. Highway 20, following alongside the Mass Pike for much of the way.
Google Maps
This southern Berkshires byway meanders through some of the most beautiful scenery and picturesque towns in Massachusetts.
The Berkshires, United States
Michael Femia/Flickr
Among them are the charming small towns of Lee, Becket, Chester, Huntington, and Russell.
The byway first opened in 1910 to accommodate the first automobiles traveling through the Berkshires.
Lee Library, 100 Main St, Lee, MA 01238, USA
cmh2315fl/Flickr
Over time, it grew into a popular tourist road for motorists and was called "the First of the Great Mountain Crossovers." It reached its heyday in the 1920s but then tourism declined once the Great Depression hit.

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With the development of the Mass Pike in the 1950s, Jacob's Ladder Trail lost even more traffic.
Massachusetts Turnpike, Newton, MA, USA
Dakota Moses/Google Map
But it certainly should not be overlooked. While Mass Pike is convenient, it's just not as scenic as this historic byway.
Between the quaint towns and the natural scenery, there are endless opportunities for adventure along, and close to, Jacob's Ladder Trail.
Keystone Arch Bridges, Chester, MA 01011, USA
Peter_01039/TripAdvisor
Pictured here is one of the bridges along the Keystone Arch Bridges Trail, conveniently found just a couple of miles off of Route 20 in Chester.
Starting in Lee, the byway travels through Becket where travelers can stop and explore its historic quarry.
Chester, MA, USA
John Phelan/Wikimedia Commons
In rural Chester, hiking is always an option along with exploring the town's historic district. After Chester is Huntington where you can stop by the country store or spend some time outdoors at Littleville Lake.
On the eastern end of Jacob's Ladder Trail Scenic Byway is Tekoa Mountain in Russell, an impressive rocky mountain with an elevation of 1,121 feet.
Tekoa Mountain, Montgomery, MA 01085, USA
Beata Grodzicka/AllTrails
If you're able to make the steep climb up the rather difficult terrain of this mountain, you will certainly be rewarded with breathtaking views from the top!

If you were to do a search for “scenic drives near me,” this byway would most certainly pop up at the top of the list!

Have you traveled along the Jacob’s Ladder Scenic Byway before? What’s your favorite back road or scenic byway in the state? Tell us in the comments! To learn more, visit the Jacob’s Ladder Trail website.

For additional scenic drives, check out these back roads and byways in Massachusetts.

And if you’d like to explore hikes around any of the places mentioned, you can find some great trails by going to the AllTrails website.

If you’re still in the mood for more Massachusetts adventures, take a look at this video about the  Top 10 Places to Visit in Massachusetts:

 

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More to Explore

Out and About in Massachusetts

Lysa Allman-Baldwin | August 15, 2023

Where can we find other scenic drives in Massachusetts?

  • The Mount Greylock Scenic Byway crosses state lines but in Massachusetts, it traverses past sites like the Ashuwillticook Rail Trail, Bascom Lodge, and Natural Bridge State Park.
  • The Route 116 Scenic Byway goes through Conway, Cheshire, Adams, Savoy, and Plainfield, just to name a few.
  • The Route 112 Scenic Byway winds from north to south from the Vermont border to the town of Huntington.

Read on to learn more about some of the many other wonderful scenic drives in Massachusetts.

Where can we find family-friendly hiking trails in Massachusetts?

  • The Chapel Brook Falls Trail in Ashfield leads to the Chapel Brook cascade and the peak of Pony Mountain.
  • The Fort Hill Trail in Eastham is a beach trail that is also great for birdwatching and picnicking.
  • Bash Bish Falls Trail in Mount Washington leads to the tallest waterfall in Massachusetts.

Read on to learn more about some of the many other family-friendly hiking trails in Massachusetts.

Where can we find the best lakes in Massachusetts?

  • Long Pond in Harwich is located along the Cape Cod Rail Trail and both are popular rest and relaxation destinations.
  • Lake Quinsigamond in Worcester is popular for watersports, fishing, sailing, and other recreational activities.
  • Spy Pond in Arlington is an excellent spot year-round and popular in the winter because it freezes and is used for ice skating.

Read on to learn more about some of the other amazing lakes in Massachusetts.

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