The Berkshires’ busiest town values sartorial discretion. Mum’s the word.

By Todd Plummer

Photography by Matthew Sussman 


There’s no shortage of historic towns in the northeast, but Great Barrington occupies its own category. In a region where many towns have centuries’ worth of history, this sleepy Berkshires enclave may not be the buzziest, it may not be the oldest, it may not be the “most” in any one category, but it doesn’t need to be—it’s got serious style chops and stands in a league of its own. 

Purchased by the Massachusetts General Court from the Mohican people in 1724 for £460, 3 barrels of cider and 30 quarts of rum, Great Barrington was named after a country retreat for English aristocrats down the road from King Charles III’s home in Highgrove. Our Great Barrington soon became an important trade stop for the area. In the mid-19th century, when trains connected it to the major cities of Boston and New York, this humble village was transformed into a summertime retreat for wealthy Gilded Age city slickers, who much preferred the fresh air of the “Berkshire Cottages” to stifling city streets. 

Great Barrington never quite had the aristocratic scene of Saratoga Springs or the ostentatiousness of Newport—instead, it was all about stylish, well-heeled folks enjoying country pursuits such as gardening, horseback riding, fishing and hiking. And today, the town has kept that quiet style. Go to Hudson if you want to be seen at brunch—go to Great Barrington if you don’t want to be seen at all. 

Of course, even the discreet types who call Great Barrington home appreciate the quality of a well-made Barbour jacket, the durability of some Hunter gumboots, the smartness of a well-fitting cashmere sweater. Because even a life lived privately, or time spent enjoying the Berkshires’ beauty should still look good, right? Right.

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