These 5 Massachusetts Towns Are the Oldest in Berkshire County, MA

We all know that if there is one thing Massachusetts has a wealth of, it's history. It's pretty common knowledge that the oldest city in the Bay State is Plymouth. However, over on the western side of the state, it's not nearly as much of a known face just how old some of these towns in the Berkshires are.

In the time that I've lived in Massachusetts over the past few years, I often find myself wanting to learn more and more about the history of every town I spend some time in throughout the Bay State. Specifically, on the western side of the state, in the Berkshires. So, why not count down the five oldest towns throughout the Berkshires. Maybe you might learn something new...

5. Sandisfield

Sandisfield is the fifth oldest town in Massachusetts. It was officially incorporated as a town in 1762. The town resides in the southeast corner of Berkshire County and as of the 2023, there is a population of 981 people in the town. Mary Seals McHenry is from there and she was president of the Women's Relief Corps in 1890, which was the largest fraternal association in the U.S. at the time.

4. Pittsfield

At the center of Berkshire County is the fourth oldest town throughout the Berkshires. Pittsfield's birthday is way back in 1761. Not only is it the largest city in the Berkshires, but also counts for being the third-largest municipality in western Massachusetts behind Springfield and Chicopee.

3. New Marlborough

New Marlborough is another town in southern Berkshire Country, right next to the fifth oldest (see above). Like Sandisfield, it also borders Connecticut. The picture you see is from The Old Inn On the Green (in case the sign didn't explain that). The town of 1,528 became incorporated in 1759.

2. Stockbridge

Stockbridge is the second oldest town in the Berkshires as it was incorporated in 1739. It's well known as one of 'America's most beautiful small towns', as well as most recently being named as one of 'America's must-visit Christmas towns'. Between its festive Main Street at Christmas celebration and the Norman Rockwell Museum, there is certainly no shortage of things to do when it comes to Stockbridge. It even gave Rockefeller Center its Christmas tree this year. And it makes sense there is so much there to do in Stockbridge since the town is about 285 years old.

1. Sheffield

The absolute oldest town in the Berkshires is Sheffield. It was incorporated in 1733. It resides to just to the west of New Marlborough. It's another town that also borders Connecticut. It's also home to the private prep school, Berkshire School. It also has a population of 3,317 as of 2023.

There you have it, Massachusetts! The five oldest towns in the Berkshires. Whether you knew that about them already or perhaps you learned something out of this, they are there to visit. Go ahead and take a drive through each one and explore a piece of western Massachusetts rich history!