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Fall is Family Time in the Berkshires

Posted on September 01, 2022Written by Cathleen King, 1Berkshire
Updated on September 20, 2023

Woman hands child an apple on the dock at Pleasant Valley with a fall backdropMass Audubon’s Pleasant Valley Wildlife Sanctuary, credit Great Sky Media

A Season to Share with Family

The change of seasons to fall brings cooler air, vibrant colors, autumnal flavors, and plentiful outdoor adventures. It’s the perfect time to gather the family and try something new together, or engage in a family-favorite activity. Fall in the Berkshires has options aplenty!  

Two people row along in boat on Mount Everett State Reservation lake with fall backdrop and foliage surround them

Mount Everett State Reservation, credit Ogden Gigli

Outdoor Adventure

The mountains and valleys of the Berkshires are home to some of the best natural treasures of Massachusetts, including the highest summit, the tallest waterfall, and a 90-mile stretch of the Appalachian Trail. The drive to the summit of  Mt. Greylock State Reservation (through November, 2023 date subject to change due to weather) is exceptional, especially as the foliage turns crimson and gold. And you can find that waterfall within the beauty of Bash Bish Falls State Park in the southern part of the county.

There is no shortage of open lands and trails throughout the Berkshires, maintained by the state and nonprofit organizations who are focused on conservation and preservation. Craft your hiking itinerary from site descriptions and trail maps found at Trustees of Reservations, the Massachusetts Department of Conservation and Recreation, and the Berkshire Natural Resources Council. If you are seeking a more curated approach, Berkshire Camino and Housatonic Heritage Walks offer myriad guided walks across the Berkshires. Each offers options for every interest and skill level, and all of them take you through breathtaking canopies of fall color.

Want to check out the views from above? Head for the zipline, mountain coaster, or aerial adventure parks at Catamount Mountain Resort, Berkshire East Mountain Resort, Jiminy Peak Mountain Resort, or Ramblewild. Feel the wind on your face as you sail above and through the fall colors. Along with an absolutely exhilarating experience, you’ll get a fresh and exciting perspective on the Berkshire landscape, especially this time of year.


Two adults assist a young child with an art project, smiling, at the Eric Carle Museum

Eric Carle Museum, credit Jim Gipe Pivot Media

Hands-On Fun & Learning

Learning about the native plants and wildlife of the Berkshires is easy to do in the fall. Take a naturalist-guided walk or paddle with Mass Audubon’s Pleasant Valley Wildlife Sanctuary, or visit the Berkshire Museum for exhibits about local flora and fauna. You can also help foster a lifelong appreciation for art and history with kid-friendly workshops and events at museums and historic sites such as the Eric Carle Museum of Picture Book Art, Hancock Shaker Village, and Historic Deerfield. Inspired by all the natural beauty, and looking to get hands-on with art? Why not check out one of the free family drop-in classes at Berkshire Arts Center and create a piece to take home.

People being pulled in a horse drawn wagon at the Hancock Shaker Village with a fall backdrop

Hancock Shaker Village, credit Ogden Gigli

Farmer’s Markets & Harvest Festivals

September and October may mark the end of the Berkshire growing season, but it’s just the start of the fairs and festivals that celebrate the harvest. In addition, several local farmers’ markets continue throughout the fall and winter. Seasonal traditions that make the Berkshires a perfect destination for you and your family include The Lenox Apple Squeeze (September 23), featuring music, food, and a children’s carnival. The Berkshire Botanical Garden Harvest Festival (October 7 & 8) includes family entertainment and children’s activities, music, pumpkin painting, and a cider press, among many other exciting offerings. The Incredible Naumkeag Pumpkin Show  (September 29-October 29) is a celebration of all things fall, with over 1,500 jack-o-lanterns and fun for all ages. Hancock Shaker Village holds a two-day Country Fair (September 23-24), including a car show, quilt show, Irish dancing, crafts, food, and live music.  As you plan your itinerary, check the Events Calendar for additional family-fun options. 

Two adults and two children walk hand in hand along gravel path at Bartlett's Orchard with a fall foliage backdrop

Bartlett’s Orchard, credit Kacey Hatch

Pick-Your-Own Farms

Who doesn’t love a crisp, warm apple cider doughnut after a playful hayride or invigorating corn maze? Check out Ioka Valley Farm for its festival-like farm display, or pick a basketful of apples with the kids at Hilltop Orchards. (Due to a late spring freeze, many of our orchards are expected to experience slim pickings – but don’t that deter you! Come for cider, donuts, and beautiful views.) Local farms and orchards are open, and their farm store shelves are loaded with bountiful fresh-off-the-vine and homemade products. Choose apples, pumpkins, pears, and late-season veggies, as well as scrumptious baked goods, jams and jellies, artisanal ciders, natural wines, and local cheeses. 

After a busy day exploring the Berkshires, settle in at a family-friendly (and maybe pet-friendly) hotel or resort such as  Hotel Downstreet, the Apple Tree Inn, or Race Brook Lodge. Each offers well-appointed accommodations, comfortable amenities, and the convenience of proximity to all you’re here to see and do. There are also scenic places to camp or to park your RV, where you can share stories from your day around an evening campfire. Stay at Fernwood Forest Campground, where you can swim and fish; Savoy Mountain State Forest, which offers cabins and two ponds; or stay lakeside at the Historic Valley Campground at Windsor Lake.

Fall for the Berkshires this year—and bring the family! Learn more about this special season in our region. 

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