How to Spend a Weekend in the Berkshires
Rolling hills, fiery foliage and winding country roads make the Berkshires one of New England’s most charming weekend escapes. Just a two-and-a-half-hour drive from Boston and three from New York City, the region (encompassing parts of western Massachusetts and northern Connecticut) has long been a favorite escape for urbanites eager to swap honking horns and crowded sidewalks for crisp mountain air and rolling hills. The locale’s small towns each offer distinct personalities: Williamstown with its world-class art museums, North Adams with its industrial edge and MASS MoCA, Lenox with its boutique-lined streets and Tanglewood concerts, and Stockbridge with its postcard-worthy Main Street, immortalized in Norman Rockwell’s Stockbridge Main Street at Christmas.
The Berkshires is a true year-round vacation destination, but fall just may be its finest hour. Hillsides burn with reds and golds, orchards brim with apples ready for picking, and cultural programming is in full swing. Festivals and community events, from the Lenox Apple Squeeze to the FreshGrass Festival, only add to the region’s seasonal charm.
A long weekend in the Berkshires offers something for everyone: a morning hike up Mount Greylock, where fiery foliage stretches across five states; an afternoon apple-picking and cider-tasting at a local orchard and an evening in Lenox, whether that means lingering over a farm-to-table dinner with local wine or catching off-season programming at Tanglewood. Read on for the best places to stay, eat and explore on a Berkshires getaway.
