Fall is Family Time in the Berkshires

A Season to Share with Family

Vibrant colors, autumnal flavors, and plentiful outdoor adventures. Fall in the Berkshires has options aplenty! It’s the perfect time to gather the family and try something new together, or engage in a family-favorite activity.

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 (open through November 1, 2024 – date subject to change due to weather) is exceptional, and once at the top, you can see Berkshire beauty from a bird’s eye view, as well as the vistas of New York, Vermont, and New Hampshire. The Veterans War Memorial Tower welcomes visitors – the light that sits atop the monument can be seen for miles.  Enjoy the breathtaking scenery and take a short hike along one of the trails. And that waterfall? It’s located within the beauty of Bash Bish Falls State Park in the southern part of the county. Once sacred to Mohican and Schaghticoke peoples, the falls makes a dramatic 60-foot drop into a stunning plunge pool. 

There is no shortage of open lands and trails throughout the Berkshires, maintained by State and nonprofit organizations focused on conservation and preservation. If you are trying to decide where to start your adventure, be sure to check out BerkshiresOutside.org, where over 550 parks, trails, and outdoor recreational locations from all across the Berkshires are listed. The site allows you to filter a search by type of adventure, and options like pup-friendly, picnicking, restrooms, and accessibility.  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.

The Ashuwillticook Rail Trail, once a railroad track, is a 10-foot wide paved trail that runs over 12 miles along Cheshire Lake. It’s a great place to walk, run, rollerblade or bike, as it is level with easy grading, and offers benches and restrooms along the way. Berkshire Bike and Board (Pittsfield and Great Barrington) offers rentals to get you moving. Bring along a picnic lunch!

For those seeking a unique foliage-related adventure, 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. Call ahead to check on availability.

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 masterpiece to take home.

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 28), featuring music, food, and a children’s carnival. The Berkshire Botanical Garden Harvest Festival (October 13 & 14) 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 27-October 27) 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 28-29), including a car show, quilt show, Irish dancing, crafts, food, and live music. Ramble Weekend (October 11-14) offers four days of family fun in Adams, from shows and train rides to RambleFest and the annual Mount Greylock Ramble! As you plan your itinerary, check the Events Calendar for additional family-fun options. 

Bartlett’s Orchard, credit Kacey Hatch

Pick-Your-Own Farms

Fall is all about flavor! 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 and house-made maple syrup, grab a few pumpkins for carving at Whitney’s Farm Market, or pick a basketful of apples with the kids at Hilltop Orchards and Bartlett’s Orchard.  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. While you are out and about, stop in a High Lawn Farm for homemade ice cream!

After all that fun and fresh air, settle in at a family-friendly (and maybe pet-friendly) hotel such as Hotel Downstreet, Race Brook Lodge, or The Blue Vista Motor Lodge. Each offers well-appointed accommodations, comfortable amenities, and the convenience of proximity to all you’re here to see and do. Prefer a quaint bed and breakfast? Find a comfy bed and ready morning meal at 33 Main, Gedney Farm, and Wilder House Berkshires. 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! Make it an annual tradition. Learn more about this special season in our region. 

For more world-class travel ideas in the Berkshires, visit berkshires.org. Learn more about visiting Massachusetts at VisitMA.com. 

Return to The Berkshires Blog