From easy and family-friendly to challenging and super-rewarding, this region of Connecticut and Massachusetts offers dozens of hiking trails for all abilities.
Even more so than Tanglewood performances and Shakespeare plays, the Berkshires is known to its admirers for its incredible scenic beauty and backcountry hiking opportunities. Through-hikers are a common sight throughout the county as the Appalachian Trail meanders through the entire region. You do not have to be looking for a three-month long adventure to enjoy this backcountry, however. It is easy to find an accessible mountain ascent to enjoy a sunset picnic upon or a challenging day hike summit with your restless dog. There is certainly no shortage of trails and stunning views to be found in the Berkshires, nor are there sites to escape into wildness.
Check out Housatonic Heritage’s hiking experiences and more information: