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10 Family-Friendly Foliage Hikes in the Berkshires

By Taylor Staubach - Berkshire Family Hikes September 16, 2020

When it comes to fall foliage, nothing beats the spectrum of colors on display in the Berkshire hills. Leaf peepers rejoice as the forested landscape erupts into shades of copper, cornelian, cranberry, gold, and every hue in between. From late September to October, this prismatic flash in the pan transforms any regular, old weekend hike into a dream-like ramble. Gazing at these fiery hills from an elevated vantage point makes us feel fixed in suspension, floating between halcyon days and the edges of change.

Here are 10  of the most accessible FOLIAGE HIKES for any age. Enjoy the fall, ya'll!


NORTH BERKSHIRE COUNTY

Niles Trail at Mountain Meadow Preserve (Williamstown/Vermont):  At the end of August, we adventured to this Trustees property and couldn't get enough of the views! We are so excited to go back and take in the view of Greylock and the Hoosac Valley during the foliage season. Check out our review here, there were mantids!

Glen Meadow Loop at Greylock Glen (Adams) Established in 2017, the newer 1.5 mile Glen Meadow Loop trail takes you around picturesque Greylock Glen. The trail is gravel, making walking a breeze. Have fun hunting for the remnants of an abandoned ski resort. The wide-open views of Greylock and surrounding hills are not to be missed. One of our favorites in all seasons, we come back here in the spring, summer, and the winter

Stone Hill Trails at the Clark (Williamstown)Part of the Clark Art Museum Complex and owned by Williams College, this is one of the most popular destinations in Williamstown for hiking and enjoying the panoramic views over Williamstown. Check out the trail map for a variety of trails, many short and easy, but all beautiful. It's hard to pick just one!

Trails at Sheep Hill (Williamstown) Both the grounds and farmhouse are open year-round to the public and a classroom is stocked with binoculars, field guides and other materials to borrow during your visit. There are two trails to choose from - the Rosenburg Ramble which takes you around the perimeter of the property, and the shorter Meadow Walk. Both of these trails offer dramatic views of the valley and surrounding mountains. Rosenburg Ramble is approximately 1- 1.5 miles. The Meadow Walk is a short, easy way to enjoy the views of Sheep Hill, and loops around the pond at the foot of the hillside.

CENTRAL BERKSHIRE COUNTY

Sacred Way Trail at Canoe Meadows Wildlife Sanctuary (Pittsfield):  One of six Mass Audubon properties in Berkshire County, Canoe Meadows is wonderful in every season. Take the Sacred Way Trail and enjoy a gentle, flat 1-mile trail winds through the sanctuary’s scenic woods, fields, wetlands, and along the Housatonic River. Open fields offer opportunities to take in fall colors. A great spot to bird watch for migrant species during the changing seasons. Fall is a great season to Go Pishing!

Wild Acres (Pittsfield):  Climb to the top of the observation tower and take in the surrounding mountain foliage. Located off of South Mountain Road in Pittsfield, Wild Acres is a 1.2 mile lightly trafficked loop neighboring the Pittsfield Airport. 

Warner Hill (Hinsdale/Pittsfield)Part of the AT, this easy up-and-back hike is 1.4 miles, ideal for families. Head through a dense evergreen forest, crunch through fallen maple and beech leaves along old stone walls, and finally to Warner Hill, where the summit offers a view of Mount Greylock on a clear day. The trailhead is right off a small parking shoulder on Blotz Road, in Pittsfield.

SOUTH BERKSHIRE COUNTY

Benedict Pond Loop Trail (Great Barrington) Located in lush Beartown State Forest, this flat 1.7-mile loop is great for all ages and offers beautiful views of serene Benedict pond. Surrounded by dense woodlands, this backdrop in fall transition is something to see.

Tyringham Cobble Loop (Tyringham) Tucked away in tiny Tyringham, this Trustees property includes a 2.1-mile loop trail running through a combination of meadow and forest. Keep an eye out for the aptly named Rabbit Rock! A well-marked trail leads to a spectacular view of the valley at the summit. See if you can spot the quaint Tyringham churchyard from the top!

JUST OUTSIDE BERKSHIRE COUNTY

Three Sisters Sanctuary (Goshen): Technically located in Hampshire County, this creative gem is well worth a side trip over the Berkshire borders. Touted as a "place where nature and art merge," one man's sensational vision is 8-acres of sculpture gardens and art installations. More of a walk than a hike, you could spend hours here trying to take it all in. In the fall, the area gets fully decorated and the surrounding woodlands are also bursting with color. The fire-breathing dragon is incredible to behold against a clear blue sky. If you're looking for an interactive, beautiful, and accessible fall walk for any age - look no further.

Check out the full list of 20 family-friendly foliage hikes at berkshirefamilyhikes.com. Follow along with all their outdoor activities & adventures on Instagram and Facebook.

Still looking for more Family Hikes? Check out our 50 FAMILY-FRIENDLY HIKES GUIDE HERE.