The Berkshires, Massachusetts Family Vacation
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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.
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....
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. ...
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. ...
Campgrounds near Benedict Pond enjoy proximity to one of the loveliest swimming holes in the area, plus a place to put in your non-motorized boat.. ...
- Tent sites
- Day use
- Bear country rules apply
The only local "castle" that welcomes wee ones, Cranwell is a bona fide vacation destination in itself, with sprawling grounds and pool. ...
Hotel / Motel
Jiminy's newfangled spring/summer Mountain Coaster raises the bar on the alpine slide genre, laying elevated tracks down the length of a ski slope and sending rider-steered cars careening down drops, around corners, and through its top-speed course....
You'll know this fabled crispy-crust, wood fired pizza place by the crowds of people spilling on to the sidewalk trying to get in....
Families like this friendly "bit of Italy in the Berkshires" for its outdoor seating (in season) and the fresh food. Parents like its local flavor, and although it doesn't have a kids menu, staff will happily adapt dishes to suit kid tastes....
Ask for a family friendly place and locals will lead you here. The busy, log-cabin style eatery appeals to kids, with its hunting-lodge décor, extensive children's menu, overflowing plates, and a fabled Mud Pie for dessert. ...
Choose your departure and arrival cities below to search for great travel deals.
Adventure and Culture in the Great OutdoorsA Family Vacation in Berkshires, MASSACHUSETTS with Babies
1.Wild 'N Wet Water & Sports RentalsWild 'N Wet Water & Sports Rentals
Lanesboro, MA 01237
2.Berkshire Scenic Railway MuseumBerkshire Scenic Railway Museum
10 Willow Creek Rd.
Lenox, MA 01240
3.Hancock Shaker VillageHancock Shaker Village
1843 W. Housatonic St.
Pittsfield, MA 01201
4.Norman Rockwell MuseumNorman Rockwell Museum
9 Glendale Rd.
Stockbridge, MA 01262
Favorite Vacation Moments
- Taking a "spirit ride"
- By heatherweller - March 08, 2008
- The Berkshires
- One of my all time favorite vacatio…