Where Are the 5 Oldest Towns in the Berkshires and How Old Are They?
With so much history throughout the entire state of Massachusetts, it's always interesting to learn about each town and cities history. While it is pretty well known that the oldest city in the state is Plymouth, over on the western side, perhaps it is not nearly as well known what the oldest towns in the Berkshires are.
As someone who has only lived in the Bay State for a little over six months now, I was curious to learn the history of our region in western Massachusetts. Specifically, in the Berkshires. So, why not count down the five oldest towns throughout the Berkshires? Maybe you might learn something new...
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 2020 census, there were 989 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.
The town that needs no introduction is the fourth oldest in 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 the southern portion of Berkshire Country, right next to the fifth oldest (see above). It, like Sandisfield, also borders with Connecticut. The picture you see is from Uppachene Falls Park. The town of 1,528 became incorporated in 1759.
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. And it makes sense there is so much there since it's about 284 years old.
The 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 with a southern border in Connecticut. It's also home to the private prep school, Berkshire School. It also has a population of 3,327 as of the 2020 census.
There they are! The five oldest towns in the Berkshires. Whether you knew that about them, perhaps you learned something out of it. Go ahead and take a drive through each one and explore a piece of western Massachusetts rich history.