What Are the 10 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 eight months now, it's always fascinating to continually learn the history of our region in western Massachusetts. Specifically, in the Berkshires. So, why not count down the ten oldest towns throughout the Berkshires? Maybe you might learn something new...

10. Williamstown

Williamstown was once called West Hoosac. It was incorporated as a town in 1765. The town is home to Williams College, as well as the Tony awarded Williamstown Theatre Festival. It has quite the unique downtown strip and it worth a taking a road trip to the northwest corner of Berkshire County for.

9. Richmond

Richmond is home to Hilltop Orchards Home of Furnace Brook Winery, which happened to be featured on NBC's 'Today' just this past fall. The town was incorporated in 1765 and is located on the western edge of Massachusetts before you hit the New York border. It has a population of 1,407.

8. Becket

The town of Becket was established back in 1765 as well. It is known for having one of the best trout streams throughout the Berkshires. It's also known for being the town where Jacob's Pillow resides, which is the historic performing arts theatre.

7. Tyringham

This town is home to Santarella, which is also known as 'The Gingerbread House'. The small town was incorporated in 1762. Former presidents, such as Grover Cleveland and Rutherford B. Hayes spent time away in Tyringham. Yo-Yo Ma, the classical musician, still has a home there. As of the last census, the town had just 427 residents.

6. 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 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.

5. Great Barrington

Visitors know the town for being sorts of a summer resort, while also being home to Ski Butternut, the fantastic ski resort. Arlo Guthrie's 'Alice's Restaurant' is actually basked on events that took place there (along with Stockbridge and Lee). Actors Chris Noth (Sex And the City) and Karen Allen (Raiders Of the Lost Ark) are also from there.

4. Pittsfield

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.

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. And it makes sense there is so much there since it's about 284 years old.

1. Sheffield

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 ten 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.