Visitors have come to the Berkshires for hundreds of years to saunter its scenic mountains. Here's a great synopsis of what the region has to offer:
Berkshires scenic hikes
Since Henry David Thoreau began visiting the Berkshires in the early 1800’s, writers, poets, musicians, artists and other luminary cultural creatives have sought inspiration from the Berkshire Mountains.
The hiking opportunities have changed little since that time, largely due to the valiant conservation efforts in the private and public sectors. The state owns and manages over 116,000 acres of public lands in the region, while private non-profits such as the Trustees of Reservations oversee such notable hiking areas as Bartholomew’s Cobble, Tyringham Cobble and Monument Mountain, to name a few.
A Berkshire visitor will surely know of the hike up Monument Mountain. For many, it is a Berkshire rite of passage. The mountain was made famous by William Cullen Bryant who penned a poem under its name and mentions a Native American woman who leaped to her death from Squaw Peak. It is also said that Moby Dick was partially inspired by a hike Melville went on here with Nathaniel Hawthorne.
The hike has numerous options from gradual ascents to steep ascents and takes from one to two hours, depending on the pace and is family friendly, though careful attention should be made at the peak where there are dangerous and steep cliffs. The views from the top are spectacular where you can see the Green Mountains of Vermont, the Catskills of New York and the northern mountains of Connecticut.
Berkshire Hills
Panoramic view of the Berkshire Hills
The Appalachian Trail (AT) runs straight through a vast majority of the county which can be explored in its entirety or in parts. Notably scenic sections run through Beartown State Forest in Monterey and South Lee, including a section running along Benedict Pond, which is great for swimming. Another wonderful section runs through Mount Washington State Forest and Jug End Reservation and if you are hiking in late July or early August, you might be so lucky to catch the wild blueberry season along this stretch.
At the very least, you will be offered incredible views of the entire southern Berkshires. One favorite side trail of the AT winds up past Race Brook Falls and is accessible from Route 41 in Sheffield. For those looking for another breathtaking waterfall experience and are looking for an easier hiking option, the nearby Bash Bish Falls which cascade 1,000 feet from above into crystal clear pools below.
Family hike in the Berkshires
For families and those seeking a more moderate hiking experience, there are some wonderful options at Kennedy Park or Pleasant Valley Wildlife Sanctuary in central Lenox, the magical Ice Glen Trail with the option to ascend up to the nearby fire tower called Laura’s Tower in Stockbridge, the dramatic Sage’s Ravine along the MA/CT border in Mount Washington State Forest, or Mount Greylock where you can even drive to the summit of this tallest mountain in the state.
For those looking for flatter and yet very remote hiking trails, the massive October Mountain State Forest in Washington, Becket, Lee, and Lenox offers plenty to explore for even the most seasoned Berkshire visitor.
