Leaf Season in The Berkshires of Massachusetts - My Family Travels

Fall foliage, great museums and Hancock Shaker village are among the winning attractions that make up the Berkshires 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: its distinctive history and its beautiful foliage.

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.

Meet the Shakers 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. This fall, light artists James Turrell partners with another former Quaker, Nicholas Mosse, to showcase Quaker pottery. Their goat yoga may be over for the season but 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. 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

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, the most commercial of the Berkshires 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.

Start around Egremont in the southern part of the county, easily reached by heading north on 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. 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.)

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.

If the family isn’t into museums, hike the nearby Appalachian Trail or take in a play at the Williamstown Theater Festival. Everyone will like the small, heated pool. In addition to college events weekends, book ahead because it’s very crowded for the Vermont foliage season.

Lee, Massachusetts at The Berkshires Foothills

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.) 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.)

Dear Reader: This page may contain affiliate links which may earn a commission if you click through and make a purchase. Our independent journalism is not influenced by any advertiser or commercial initiative unless it is clearly marked as sponsored content. As travel products change, please be sure to reconfirm all details and stay up to date with current events to ensure a safe and successful trip.

Comment on this article

This site uses Akismet to reduce spam. Learn how your comment data is processed.