Start your day in Stockbridge with breakfast at the Main Street Cafe (413-298-3060). While you are enjoying your waffles or omelet, know that you are (sort of) inside a painting by Norman Rockwell; the artist spent the last 25 years of his life in Stockbridge, and his portrayal of Main Street has become an iconic image of American small-town life. After breakfast, take a short, scenic drive up Route 183 to see the canvas version at the Norman Rockwell Museum (413-298-4100, nrm.org), the world’s largest collection of his work. Marvel at the detail in Rockwell’s original paintings as well as the room devoted to his covers for The Saturday Evening Post. Spend some time walking the scenic grounds, enjoying the outdoor sculptures and touring Rockwell’s studio. read more

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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