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The Berkshires, Massachusetts Family Vacation

Adventure and Culture in the Great Outdoors

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At a Glance

Lush mountains, fresh air, crystal clear lakes . . . what's not to love? The Zen of the Berkshires (legend has it that just-so rock formations give the place a sort of cosmic feng shui) has been drawing crowds since the Guilded Age, when rich folks arrived with their newly built family "cottages" (mansions to we common folk). Families still flock here, now to enjoy the mix of plentiful culture (much of which can be enjoyed casually alfresco) as well as more adventurous outdoor fun. It's a blend unique to the Berkshires, where families can hike the Appalachian Trail, ride horses, or whitewater raft by day and throw a Frisbee at an outdoor classical musical concert on the lawn at Tanglewood by night. Don't miss the plentiful shops, restaurants, and ice cream stores that dot the landscape of the cute little Berkshire towns—lapping up culture never tasted so good.

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Suggested Trip Plan by Age

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Berkshire Scenic Railway Museum

Lenox

Good for Toddlers & Pre-K

***** see all ratings

Scenic rides aboard this mobile museum are in vintage 1920s cars, pulled behind a diesel engine run by an overalls-clad engineer. Excursions are the perfect length for little riders—about 30 minutes to Stockbridge, with a quick stop midway in Lee....

  • Special Collection

  • Historical Landmark

  • Roadside Landmark

  • Train

Hancock Shaker Village

Shaker Village

Good for Babies

*** see all ratings

If not for the cars buzzing by on Route 20, you'd think you'd stepped into a completely different era. Ye Olde Village has vintage buildings showing how the Shakers used to sleep, eat, and do other things. ...

  • History Museum

  • Historical Landmark

Norman Rockwell Museum

Stockbridge

Good for School-Age Kids

***** see all ratings

Paintings at this charming museum aren't just art: they're stories. Familiar even to kids, Rockwell is a perfect introduction to painting. The artist's intricately crafted details make viewing feel like you're peering through the window of a dollhouse. ...

  • Art Museum

  • Special Collection

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Adventure and Culture in the Great Outdoors

A Family Vacation in Berkshires, MASSACHUSETTS with Babies
  1. 1.

    Wild 'N Wet Water & Sports Rentals
    Wild 'N Wet Water & Sports Rentals
    Rt. 7
    Lanesboro,  MA  01237
    413-445-5211
    42.49417972222222 -73.23848194444444
  2. 2.

    Berkshire Scenic Railway Museum
    Berkshire Scenic Railway Museum
    10 Willow Creek Rd.
    Lenox,  MA  01240
    413-637-2210
    42.350495 -73.2448038888889
  3. 3.

    Hancock Shaker Village
    Hancock Shaker Village
    1843 W. Housatonic St.
    Pittsfield,  MA  01201
    413-443-0188
    42.43148083333333 -73.33409388888889
  4. 4.

    Norman Rockwell Museum
    Norman Rockwell Museum
    9 Glendale Rd.
    Stockbridge,  MA  01262
    413-298-4100
    42.28135888888889 -73.31190194444444
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Favorite Vacation Moments

Taking a "spirit ride"
By heatherweller - March 08, 2008
The Berkshires
One of my all time favorite vacatio…