The Berkshires Blog

Fall Hikes in the Berkshires: From High Country to Low Country

While the foliage is certainly the star of the show this time of year, the sum of all the little things that go along with the change in season certainly plays an award-winning supporting role. From the feel of layering up in your fleeces and hard-shell jackets, to the taste of a crisp, in-season apple on a blustery and raw mountain summit, autumn brings with it more than spectacular color. These are some of our favorite hikes in the Berkshires to discover all that fall in the outdoors has to offer.

With over 16,000 acres to explore, most people catch views October Mountain State Forest’s (the largest state forest in Massachusetts) foliage from the valley below. But atop this high plateau above the Housatonic River Valley, you’ll find a labyrinth of rolling trails, including a section of the famed Appalachian Trail and the 2.7 mile Washington Mountain Marsh Interpretive Trail. Whether you’re looking for the perfect family hiking adventure, or are in town for a fall wedding in the Berkshires and only have a short window to plan an outdoor excursion, the Washington Mountain Marsh Interpretive trail delivers a combination of spectacular views, ecological diversity and Berkshire history with nine marked areas and location descriptions along the way. While the foliage at this elevation changes early, the vistas along the marsh are always changing, which makes it a great hike any time of the year. You’ll find the Washington Mountain Marsh Interpretive Trail along West Branch Road inside the State Forest. You can find more information on October Mountain State Forest and the interpretive trail here.

At the southern end of Berkshire County you’ll find one of our region’s more unique natural areas. Bartholomew’s Cobble features a pair of twin, rocky knolls formed as a corral reef over a half billion years ago. Today the archaeological attraction sits along the Housatonic River and bucolic rolling hills of South County. Beginning at the Trustees of Reservations’ Visitor’s Center on Weatogue Road in Sheffield, you’ll find five miles of trails varying from easy meadow loops, to a moderate climb up Hurlburt’s Hill. The 0.8 mile walk to the Hurlburt’s Hill overlook takes hikers 400 feet up an old tractor path, through a hardwood forest, through a meadow and to a wide-open view directly on the Massachusetts and Connecticut border. This walk is perfect for kids, first dates and big groups, who can split up to enjoy the trails around the cobble and Hurlburt’s Hill, and then meet back at the Visitor’s Center. More information is available at the Trustees of Reservations.

It’s difficult to talk about any “favorite hikes” list without mentioning Mount Greylock and since it’s especially beautiful this time of year, we’ll propose a new look at it. As the highest summit in the state at 3,491 feet, it’s broad shoulders give 70 miles of diverse trails and its Scenic Byway auto road to the summit allows even non-hikers to experience the beauty of the 90 mile, four-state views. For experienced hikers in search of a challenging adventure, head for the summit via the Appalachian Trail, beginning at Outlook Avenue in Cheshire. The 6.8 miles to the top will leave even seasoned hikers huffing, but those moments of rest simply provide the opportunity to take in the scenic views around you. This time of year, you will most likely see every shade of foliage — from early tints, to full peak and winter grey — as you ascend. That’s also a sign of the temperature gradient which you’ll experience, so be sure to dress in layers and bring gloves, a warm hat and waterproof jacket to battle any elements you may encounter.

Go forth and explore this fall. You won’t regret a single minute you spend on the trails of the Berkshires, when the leaves are changing and the cooling temperatures lead to rosy cheeks and refreshing views.