It’s tempting to declare fall the best time of year to visit western Massachusetts: The leaves are changing, the air is cool, and the sun’s incandescent beams bounce off the arboreal reds, oranges, purples, and yellows.
But the region is perfect pretty much year-round, even in the dead of winter—as resident James Taylor sang in 1970, praising the snow along “the Turnpike from Stockbridge to Boston,” how “the Berkshires seemed dreamlike on account of that frostin’.”
Western Mass. has long held a special allure, drawing artists and academics to its remote, natural beauty as early as the 19th century, and later luring weekenders and vacationers up from New York City and out from Boston. “Snow trains” ran from Grand Central Station and New Haven during the winters, carting skiers and other outdoor enthusiasts (and such trains might run again).
The region’s mix of pastoral splendor and proximity to those major hubs shaped it over time, drawing a host of notable figures as varied as Norman Rockwell and Herman Melville, a bevy of children’s book authors (Dr. Seuss was a native), and a share of tycoons seeking to build grand country estates not too far from their city homes. Many of those estates live on as museums and tourist curiosities, and you can even stay in a few of them.
This guide will help you make the most of your next visit to Western Mass., with an introduction to quaint towns, intel on where to stay and what to do, and even a story about the best ways to behold the bucolic landscapes. —Tom Acitelli
Writers: Tom Acitelli, Mary Meisenzahl
Editors: Tom Acitelli, Sally Kuchar, Mercedes Kraus, Mariam Aldhahi
Photo director: Audrey Levine
Photographer: Tony Luong
Copy editor: Emma Alpern