Distance 50 miles
Lenox — Lee — Otis — Great Barrington — Stockbridge
This drive has a good mix of towns with historic houses, steepled churches and village greens. But a favorite section in the fall is Route 183 beside the Housatonic River, where the water reflects the leaves.
On 183, visit the Berkshire Mountain Bakery. It supplies loaves to gourmet restaurants throughout western Massachusetts and Connecticut. Farther along, visit the Norman Rockwell Museum, whose collection includes the artist’s famous Saturday Evening Post covers.
Work off breakfast with a climb at Monument Mountain (zip down Route 7, between Stockbridge and Great Barrington). When Herman Melville and Nathaniel Hawthorne did this 3-mile hike in 1850, they had time to hash out some plot points of what would become Moby-Dick. The views, as Melville discovered, are that inspiring.
Route: From Lenox town center, Rte. 183 N to Rte. 7 S.; mi. to Rte. 20 E; 11 mi. to Rte. 8 S; 5.5 mi. to Rte. 23 W; 16 mi. to Rte. 7 N; 1 mi. to Rte. 183 N; 14 mi. to Lenox.