The Metacomet-Monadnock Trail is a 114-mile-long (183 km) hiking trail that traverses the Metacomet Ridge of the Pioneer Valley region of Massachusetts and the central uplands of Massachusetts and southern New Hampshire. Although less than 70 miles (110 km) from Boston and other large population centers, the trail is considered remarkably rural and scenic and includes many areas of unique ecologic, historic, and geologic interest. Notable features include waterfalls, dramatic cliff faces, exposed mountain summits, woodlands, swamps, lakes, river floodplain, farmland, significant historic sites, and the summits of Mount Monadnock, Mount Tom and Mount Holyoke. The Metacomet-Monadnock Trail is maintained largely through the efforts of the Western Massachusetts Chapter of the Appalachian Mountain Club (AMC). Much of the trail is a portion of the New England National Scenic Trail.

The Metacomet Ridge, Metacomet Ridge Mountains, or Metacomet Range of southern New England is a narrow and steep fault-block mountain ridge known for its extensive cliff faces, scenic vistas, microclimate ecosystems, and rare or endangered plants. The ridge is an important recreation resource located within 10 miles (16 km) of more than 1.5 million people, offering four long-distance hiking trails and over a dozen parks and recreation areas, including several historic sites. It has been the focus of ongoing conservation efforts because of its natural, historic, and recreational value, involving municipal, state, and national agencies and nearly two dozen non-profit organizations.