The Berkshires Blog

The Berkshires, An Ideal Location for a Family Getaway

By Kelly Bevan McIlquham

When looking to schedule your next family vacation, you need look no further than the Berkshires of Massachusetts. “I think if I were to be here for a weekend I would want to make sure my children saw one theater piece, went to Jacob’s Pillow (Becket) and Tanglewood, strolled through one of the museum’s and then experienced a hike at somewhere like Monument Mountain or Gould Meadow,” said Kate Maguire, a Berkshire resident, mom of three grown children and Artistic Director and CEO of the Berkshire Theatre Group. Having difficulty narrowing her list down for families Maguire added “ … or visit Arrowhead or Chesterwood to see the Lincoln statue.”

Add to that extensive “weekend list” kayak at a local lake; bike the Ashuwillticook trail; attend a street festival; and sample some local fare at a farmers market, just to name a few — and you’ve got a recipe for a fun-filled family getaway that will have your kids talking about the experience for years to come.

Where to Stay

Not only does the Berkshires have your family fun covered, they’ve got a mix of lodging options to fit your family’s needs and budgets. Be it a bed and breakfast, local resort, campground, rental property or hotel, you can find one to accommodate your family from the rolling hills of Williamstown to the quaint streets of Great Barrington and anywhere in between.

For Barrington, Rhode Island mom, Jackie Hennessey, and her large extended family the ideal setting was a large farmhouse rental tucked away in a quiet neighborhood in Lenox, just a hop, skip and a jump from Tanglewood. “We wanted a place to congregate and relax like we have in the past at places like Martha’s Vineyard. We like to play games and have our Family Olympics), in between exploring the area,” said Hennessey.  “We had heard the Berkshires were similar with lots to do and a variety of activities so we tried it.”

Start your lodging search here.

Plenty of fun for the whole family

During her winter trip with her two children then 9 and 12, in-laws and nieces and teen nephews, exploring meant skiing, taking in some art at local coffee shops, visiting the Norman Rockwell Museum in Stockbridge and stopping at one of the region’s hidden family gems, the Museum of Animagic in Lee. “The museum was small in size with big rewards,” Hennessey raved. “It was very interactive and we learned a lot about Eugene Mamut (Oscar-winner and museum owner). It was very impressive.”

Hennessey was equally impressed with the Norman Rockwell Museum.“I had heard about it, but didn’t know how much there was for kids,” she said. “It’s actually amazing how much there is at those types of museums for them.  My kids recognized a lot of the photos and my daughter spent a lot of time in the Art Zone doing a project.”

Summer fun

Though her visit came in the winter, Hennessey can see herself returning for a summer getaway in the future. “I’d like to take in a concert at Tanglewood and maybe take some small hikes and explore the outdoors,” she said. “Maybe see some theater and visit some more museums, too.”

Those concerts, museums, outdoor adventure and family theater opportunities aren’t limited to Lee and Lenox. During the warmer months, many of the ski resorts like Catamount in South Egremont, Bousquet in Pittsfield and Jiminy Peak in Hancock turn their attention to their Adventure Parks with ziplines, rope bridges, climbing structures and more for families to enjoy. The new Ramblewild opening this summer in New Ashford will provide a new adventure in the trees for families visiting the area.

Area museums like the Berkshire Museum in Pittsfield, The Clark Art Institute in Williamstown and MASS MoCA in North Adams and historical sites such as South Berkshire County’s Bidwell House, Naumkeag, the Ashley House and North Adam’s Natural Bridge State Park come alive with Family Days, new exhibits and outdoor festivals, concerts and activities during the summer months. Local beaches and parks are bustling with activity and feature outdoor stages for free summer music series performers, and family theater opportunities once limited to indoor theater venues move outdoors at places like the Williamstown Theatre Festival up north and Shakespeare & Company and The Mount in Lenox.

Downtowns and food

And then there’s the food prepared by world-class chefs and local fare throughout the county to enjoy. Yum. But talking about it in just a paragraph wouldn’t do it justice, you’ll have to taste it yourself. See a list of restaurants here and visit and become a fan of the TasteBerkshire facebook page.

So whether you choose to spend your time in North, Central or South Berkshire County, or spread your time throughout the Berkshires, you can be sure there will be ample opportunity for your family to explore and indulge in all the region has to offer. Even better, as Hennessey found out, the majority of lodging accommodations in the Berkshires allow you and your family a place to relax and unwind away from the hustle and bustle of the seasonal activities, but they remain close enough, so you’re just a hop, skip and a jump away from enjoying the family fun. “The fact that there was a downtown close by that we could go and explore, shop, stop at a local coffee shop and participate in activities was great,” Hennessey said. “Just knowing those things are there and the conveniences were close by, but we weren’t in the middle of it was nice.”


Kelly was born and raised in the Berkshires and is now living and raising her three children, Max, McKenna and Shea, with her husband Mark in Hinsdale. She is the founder of Berkshire Family Focus, the one-stop online source for family activities, events, information and more in Berkshire County.