From Manhattan (3 hours): Take the Major Deegan Expressway or the Henry Hudson Parkway to the Saw Mill River Parkway, then proceed on the Taconic State Parkway. Take the exit marked "Hillsdale, Claverack, Route 23" and follow Route 23 East to Great Barrington. Turn North on Route 7 and continue through Stockbridge. At the first traffic light past Stockbridge, turn left onto Route 7A into Lenox.
From Boston (2 1/2 hours): Take the Massachusetts Turnpike to Exit 2, marked Lee. Follow Route 20 West about 4 miles beyond Lee to the second traffic light. Turn left on to Route 183 into Lenox.
From the Hartford/Springfield Area (75 minutes): Go North on Route I-91 to the Massachusetts Turnpike West; then proceed by the directions for traveling from Boston.
From Albany (1 hour): Go East on the New York Thruway to the Massachusetts Turnpike Exit 2; then proceed by the directions from Boston. Or take Route 20 all the way from Albany to its intersection with Route 7 in Pittsfield. Follow Route 7 South to Route 7A into Lenox.