If mountains were children, the Berkshires would be just the right size -- big enough to be exciting, but not enough to get into any real trouble. The green hills of Western Massachusetts are a wild fantasyland of rushing rivers and plunging gorges, cutting between rounded peaks covered in brilliant foliage every fall. But the fact that the area is a three-hour drive from both New York and Boston has injected a healthy dose of civilization among the hills. A century ago, upscale city-dwellers and artists began building their summer cottages out here. Famous residents included novelists Herman Melville and Edith Wharton and Lincoln Memorial-creator Daniel Chester French, all of whose homes are now open to the public for tours. Nowadays, the area is known as a summer arts playground to a new generation of expat urbanites, anchored by the Boston Symphony Orchestra's seasonal home at Tanglewood, and festivals including the Jacob's Pillow Dance Festival, the Williamstown Theatre Festival, and Shakespeare & Company's annual season of plays.
Despite its wild topography, the Berkshires are easy to get around -- Route 7 cuts down the middle, hitting all of the major town centers in an easy hour-and-a-half drive from the Vermont border to Connecticut. The ends of the highway are anchored by the cultural centers of Williamstown to the north and Great Barrington to the south. In the middle is the large, but somewhat unsightly town of Pittsfield; the quaint but somewhat snooty village of Lenox (home of Tanglewood); and the picturesque but somewhat touristy town of Stockbridge, home to the popular Norman Rockwell Museum. It's no surprise, perhaps, to find out Rockwell once made his home here -- the landscape is classic New England, with white-steepled churches and clapboard homes surrounding perfect town greens. If general stores and antiquing are your thing, you'll find plenty of opportunities while driving along Route 7 and the backgrounds snaking their way through the hills.
Despite the popularity of the region when the summer arts festivals are in full swing, this is very much a four-season destination for families. Several museums and other attractions cater specifically to kids, and even historic B&Bs and tony restaurants are used to accommodating children if not welcoming them with open arms. For active kids and teens, outdoor attractions are easy to find, with canoeing, hiking and horseback riding catering to all levels of outdoor ability. And even the region's many music and theater companies run special programs for families to experience culture without pretension. Add it all up, and this may very well be one of the best places to take a vacation with the family.
Berkshires Family Vacations
Berkshires Family Vacations

Families will love:
- Quaint and picturesque, classic New England towns
- Four-season, outdoor family adventure
- Summer art festivals and concerts at Tanglewood
Written by Michael Blanding
Read more about Berkshires AttractionsBest Berkshires Family Hotels
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All rights reserved. This file may be downloaded for personal
use only. Other copying or reproduction is expressly prohibited.





