The Berkshires (pronounced as "berk-shurs" or "berk-sheers") are a branch of the Appalachian Mountains, centered in Western Massachusetts (with portions located in the adjacent states of Vermont, New York, and Connecticut). They are often referred to as the "Berkshire Hills." The Berkshires are a popular tourist attraction and vacation getaway, serving the same function in relation to Connecticut and Massachusetts that the Catskills do in New York and the Poconos for Pennsylvania. With numerous trails, including part of the Appalachian Trail, large tracts of wilderness, parks like Kent Falls, Berkshire Botanical Garden and Hebert Arboretum the Berkshires are very popular with nature lovers. The range includes Bash Bish Falls, the tallest waterfall in Massachusetts.

Northwestern Connecticut features the covered bridges of Kent and West Cornwall, spectacular fall folliage along the Housatonic River valley and the quiet woods of the aforementioned Appalachian trail.