A 90-mile swath of the Appalachian Trail cuts through the Berkshires. You'll also find hundreds of miles of trails elsewhere throughout the area's forests and parks.
Appalachian Trail. You can walk part of the Appalachian Trail on a moderately strenuous stretch that leads to Ice Gulch, a gorge so deep and cold that there is often ice in it, even in summer. Follow the Ice Gulch ridge to the shelter and a large, flat rock from which you can enjoy a panoramic view of the valley. The hike takes about 45 minutes one-way. Trailhead on Lake Buel Rd., about 100 feet northwest of Deerwood Park Dr., Great Barrington, Massachusetts. www.appalachiantrail.org.
Bartholomew's Cobble. This rock garden beside the Housatonic River (the Native American name means "river beyond the mountains") is a National Natural Landmark, with 5 miles of hiking trails passing through fields of wildflowers. The 277-acre site has a visitor center and a museum, as well as the state's largest cottonwood trees. 105 Weatogue Rd., Sheffield, Massachusetts, 01257. 413/229–8600; www.thetrustees.org. $5. Daily dawn–dusk.
Monument Mountain. For great views with minimal effort, hike Monument Mountain, famous as a spot for literary inspiration. Nathaniel Hawthorne and Herman Melville trekked it on August 5, 1850, seeking shelter in a cave during a thunderstorm. There they discussed ideas that would become part of a novel called Moby-Dick. While poet William Cullen Bryant stayed in the area, he penned a lyrical poem, "Monument Mountain," about a lovesick Mohican maiden who jumped to her death from the cliffs. Most hikers find the 2½-mile loop an easy stroll. Trailhead at parking lot on west side of U.S. 7, 3 miles north of Rte. 183, Great Barrington, Massachusetts. 413/298–3239; www.thetrustees.org.