Family Vacations to The Berkshires, Massachusetts

Shelburne Falls, The Berkshires, Massachusetts
Shelburne Falls (courtesy, MOTT)

The Berkshires Highlights

  • Watch beavers at work at Pleasant Valley Wildlife Sanctuary.
  • Learn about the Shaker way of life at Hancock Shaker Village.
  • Ride vintage trains at the Berkshire Scenic Railway Museum.
  • Dig for dinosaurs at the Berkshire Museum.
  • Climb (or drive) to the top of Mount Greylock and see five states.
  • Paddle the Housatonic River and walk the trails at Bartholomew's Cobble.

Stretching from Massachusetts' southern border with Connecticut to the northern boundary with Vermont, the Berkshires, a region of hills laced with forests and rivers, form the far-western flank of the state. It may take only two hours to drive the length of the Berkshires, but the region features a wealth of museums, parks, nature preserves, and cultural events to keep the family going for a week or longer. Good bases for exploration are the Revolutionary-era towns of Lenox and Stockbridge and the commercial hub of Pittsfield.

In Lenox, part of the central Berkshires, young kids will like the Pleasant Valley Wildlife Sanctuary's nature trails through forests, meadows, and wetlands, where you might even catch a glimpse of industrious beavers. Train enthusiasts can ride aboard vintage cars (Memorial Day until the end of October) for an excursion from Lenox to Stockbridge at the Berkshire Scenic Railway Museum. With older kids, take in a play by the Bard at Shakespeare & Company. Arrive early to stroll the nature trails and enjoy the free music and dance performances before curtain time. For world-class music under the stars, spread a blanket on the lawn at Tanglewood, summer home of the Boston Symphony Orchestra.

A quintessential New England town, Stockbridge is home to the Norman Rockwell Museum. All 321 Saturday Evening Post covers produced by Rockwell are on display from the end of May through the end of January 2007. At the Hancock Shaker Village, a living history museum on 1,200 acres near Pittsfield, kids weave on a loom, use quill pens as part of their 19th-century school session, and milk Mary Jane, a replica of a Holstein cow while learning about the Shaker way of life. At Pittsfield's Berkshire Museum, where kids can touch starfish in a tank and dig in a sandpit for dinosaur bones, a full-size stegosaurus named Wally greets visitors.

For an adventure in the northern Berkshires, drive or hike to the top of Mount Greylock, the tallest point (3,491 feet) in Massachusetts, which features a view of five states. At the Clark Art Institute in Williamstown, kids learn about the paintings at computer stations and by reading the "Looking Carefully" cards. Children make their own art at Kidspace, a free gallery in the massive main Massachusetts Museum of Contemporary Art (MASS MoCA) building in North Adams, devoted to creative exhibitions that challenge and increase youngsters' appreciation of contemporary art.

In the southern Berkshires, walk through Bartholomew's Cobble, a nature reserve with forests, wildflowers, and migrating birds, or paddle the winding Housatonic River with a naturalist guide on summer Sundays. In the town of Beckett, throughout the summer, the Jacob's Pillow Festival offers a range of dance performances, some of which are geared to young audiences.

In winter, ski, snowshoe, and sled in the Berkshires at Butternut, Catamount, Jiminy Peak, and other family-friendly recreation areas and resorts.

Tip: Fall colors peak in late September and October when the Berkshires are ablaze in gold and red.

Recommended Side Trips: Boston, New York City, Albany (New York)'s resident family expert Candyce Stapen has written the book on family travel, having authored some 1,400 travel articles and 27 books, 26 of them on family travel. She is the winner of the 2004 "Caribbean Travel Writer of the Year for North America" award and a three-time winner of the Society of American Travel Writers' Lowell Thomas Travel Journalism award. Her articles have appeared in publications including Nick Jr , FamilyFun , Parents , Better Homes & Gardens , Conde Nast Traveler , National Geographic Traveler , and the Family Travel Network , among others. Her book, the National Geographic Guide to Caribbean Family Vacations is available from

Published: 3 Oct 2007 | Last Updated: 23 Sep 2010
Details mentioned in this article were accurate at the time of publication



Sign up to Away's Travel Insider

Preview newsletter »