Hike in the footsteps of literary giants like Herman Melville and Nathaniel Hawthorne, who spent time on the summit of Monument Mountain’s 1,642-foot Squaw Peak outside Great Barringtonin the Berkshires. From the top of cliffs, gaze upon a glorious landscape, including Mount Greylock and New York’s Catskills. Using the Hickey, Squaw Peak and Indian Monument trails from the Route 7 trailhead, hikers can navigate a nearly 3-mile loop along a former carriage road, by a jumbled boulder field and under cliffs. There are some abrupt pitches, but those Housatonic River Valley vistas are worth it. (thetrustees.org)

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