Great Barrington

Great Barrington, Massachusetts

The largest town in the Southern Berkshires, Great Barrington is a destination in itself with its ample natural beauty and small town charm. Although still a fairly well-kept secret, it has been growing in popularity in recent years thanks to an influx of unique and trendy businesses, drawing in young New Yorkers looking to escape from the city for a long weekend.

The cozy brick town is vibrant and rich in culture, and after wandering through downtown you’ll come across countless restaurants, bars, shops, galleries, and other attractions of a quintessential American Main Street.

Great Barrington also has a wealth of history tucked away within its streets. Railroad Street, for example, is one of the oldest streets in the United States still in existence. Main Street, on the other hand, was the first American street to receive electric lights. Take some time to wander the streets on your own and immerse yourself in more of the history that has helped shape Great Barrington into the town it is today. 

If history isn’t quite your thing and you’re in need of another reason to visit Great Barrington, look no further than it’s stunning natural surroundings no matter what time of year you’re visiting. With hundreds of hiking and walking trails easily reached from the center of town, there are plenty of ways to explore the region and discover why the Berkshires has always been a haven for nature lovers.

For a mellow afternoon, start at Brooks Pharmacy and take a relaxing stroll along the public footpath of the Housatonic River as it winds its way through town and up to the village of Housatonic.

If you’re looking to break a sweat with more of a challenge, then Monument Mountain is an absolute must! The demanding ascent brings you to the peak at almost 1,800 ft above sea level, with breathtaking views of the lush green landscapes, rivers, and foothills below.

And if you happen to be visiting in the winter, Ski Butternut to the east of town provides over 10 acres of trails with 11 ski lifts, making it the perfect place to hit the slopes!

No matter what your travel style is, Great Barrington has something to offer, so be sure to make a stop in town on your next Berkshires getaway and see for yourself why this is one of the most popular towns in the entire region!