Enjoy The Berkshires With Kids - My Family Travels

Enjoy the Berkshire Mountains with kids thanks to Western Massachusetts’ verdant scenery, many great (and small) musuems and the unique Hancock Shaker Village. Whether you go by mass transit (see our Berkshire Flyer train to Pittsfield story) or drive, the Berkshire Mountains promise a fun, low-key family vacation.

Located in Western Massachusetts, the Berkshire Mountains are one of the most scenic parts of New England. These activities show off the unique charm of this region for kids: its distinctive history and its beautiful foliage at any time of year.

Goat yoga on the lawn at Hancock Shaker Village in Massachusetts
Goat yoga takes place weekends on the lawn at Hancock Shaker Village in Massachusetts.

Plan ahead for the major long weekend holidays, however. Rates rise and crowds descend in autumn, too, when peak foliage arrives. There are a lot of B&Bs, vacation rentals and roadside motels to accommodate families of almost any budget.

Meet the Shakers With Your Kids In The Berkshires

The Hancock Shaker Village (1843 Housatonic Street, Pittsfield, MA 01201, 413/443-0188) is open daily 11am-5pm from May through October, although due to the pandemic, hours will be irregular after Labor Day. Step back to an era when the Shaker community believed in “hands to work and hearts to God.”

Twenty restored buildings are open for touring, including a unique round stone dairy barn with milking demonstrations daily. Unique to the Berkshires, there’s replica 1820 schoolhouse, and a dwelling house where up to 100 Brothers and Sisters lived in separate quarters. Tour buildings where Shakers lived, worked, and practiced the concept of creating a perfect society — one they hoped would inspire the rest of the world to abandon war, capitalism, and inequality. Private tours for up to six are available with advance reservation and cost $250.

There’s so much to see on your own in the Berkshires. Pick up a “Family Activity Book” and allow some work time in the Family Discovery Room located in the 1910 Barn. Museum-goers will find the museum of everyday farm artifacts and traveling artist shows to be quite fascinating. Check on their popular goat yoga classes and try to book one. If not, the cafe will still be open.

Ride the Rails in The Berkshires

Egremont countryside with corn field and barn in background.
Egremont is known for its dairy farms and its gentlemen farmers, so the views and homes are beautiful.

The Berkshires Scenic Railway Museum (10 Willow Creek Rd, Lenox, MA, 01240, 413/637-2210) operates the colorful Hoosac Valley Train ride between Lenox (the classic station is a small train museum) and Stockbridge, through September and, sometimes, longer for the holidays.

There are two tour options. Enjoy a 90-minute, round trip excursion on a 1950’s locomotive to enhance your experience of Western Massachussetts.  A 45-minute ride is also available for those with shorter attention spans; this could be another way to sneak a peek at fall foliage.

Road Tripping Around Great Barrington With Kids

Outside fountain at the Clark Art Institute in Williamstown, Massachusetts
Outside fountain and fish sculpture are featured at the Clark Art Institute in Williamstown, Massachusetts.

Verdant fields and pasture land full of cattle and sheep surround the fun village of Great Barrington. When touring the Berkshires with kids, it’s obvious that it’s the most commercial of towns. The affluent, post Hippie enclave is located in the Housatonic River valley with several rivers flowing nearby — perhaps why it became the first Main Street in the U.S. to have electric lights. The town was home to activist W.E.B. Du Bois and is currently the residence of actress Karen Allen, who starred in the “Indiana Jones” film franchise and runs a fiber arts store on Railroad Street.

Definitely stop here and take time to explore. Sheffield was settled in 1725 and is The Berkshires oldest town, with the highest proportion of antiques dealers and active farms in the region. 

Route 7 North leads to the famous artist enclave at Stockbridge. The Norman Rockwell Museum (9 Glendale Road, Route 183,  Stockbridge, MA, 01262, 413/298-4100) features the greeting card style, picture-perfect New England that Rockwell loved to use in his illustrations for the Saturday Evening Post and other assignments. Look for the ever-changing special exhibitions, engaging programs such as outdoor movies and more goings-on around the scenic 36-acre campus. (Closed Wednesday.)

Fall and Winter Adventures In The Berkshires With Kids

Fall brings changing leaves and thousands of slow-moving vehicles packed with leaf peepers. Winter brings snow lovers and families who want to start off their kids with the Berkshires snow sports. Fewer crowds and value prices make winter the better choice for families.

Start your snow season trip around Egremont in the southern part of the county. From Great Barrington, head north on scenic Route 41 from New York State and the Mount Washington State Forest. Go West at Route 23 and the narrow, winding country road will take you to the Catamount Ski Resort.

Their aerial adventure park, a combination of ropes, bridges, harnesses, trees, barrels and more, runs right through the canopy of trees. Take advantage of the stunning foliage views if you’re not afraid of heights. Check the Catamount website for details; the minimum age is 7 years and it’s open weekends through early November.

Drive Route 41 East (also called Maple Avenue) northeast to Great Barrington. The Butternut Ski Area and Tubing Center, a small, family-favorite resort outside of town, opens in December for the ski season. Route 7 South of town leads to Sheffield.

Older Kids Love Williamstown, Gem of the Berkshires

Take the family to the Clark Art Institute (225 South Street, Williamstown, MA, 01267, 413/458-2303.) As a research institution affiliated with Williams College, the Clark’s extensive collections include European and American painting, sculpture, and decorative arts from the Renaissance to the early 20th century. Perhaps the kids will want to take a campus tour at nearby Williams or join an outdoors tai chi class, gallery talk or just wander around the tranquil grounds themselves.

If you base yourselves at one of the Berkshires inns, you will be in the prime area for leaf peeking. We suugest the Williams Inn (Willamstown, MA, 01267, 413/458-9371.) This sleekly contemporary inn has 64 guest rooms whose design is reflective of local area farmhouses. While maintaining its charm, it’s environmentally sustainable and high-tech in its amenties.

The Maple Terrace Motel is another popular option, within walking distance of The Clark (555 Main Street, Williamstown, MA, 01267, 413/458-9677). Book a top value guest room or a larger family apartment with kitchen facilities. Everyone will like the small, heated pool that tries to stay open for three seasons. In addition to college events weekends, book ahead because it’s very crowded for the Vermont foliage season.

If the family isn’t into museums, hike the nearby Appalachian Trail. Depending on local support to finance a new theatrical season, take in a play at the Williamstown Theater Festival.

Lee, Massachusetts Is The Berkshires For All Ages

Black Swann Inn exterior, inn in Lee, Massachusetts
The waterfront Black Swann Inn is a very nice inn in Lee, Massachusetts.

Nearby Lee, Massachusetts is home to the modern MASS MOCA, a fun, big and colorful museum that will baffle young art lovers. (Closed Tuesday.) It’s a great town to walk around in with fun shops and unusual artisan galleries.

Our favorite base here is the Black Swan Inn (435 Laurel St, Lee, MA, 01238, 413/243-2700). In addition to rooms with views over the beautiful Lake, the friendly staff offer guests pontoon and kayak rentals and a highly regarded Indian restaurant named MINT.

Let us know what activities you plan for your Berkshires weekend. (Many people choose to spend a lifetime there — with good reason.)

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