Compared to the northern Berkshires , the towns along the southern half of the mountain chain have a more sophisticated feel. The mountains themselves are smaller and have a smoother, gentler appearance than their northern neighbors, and the area has long been a country-getaway destination for wealthy urbanites from New York City  and Boston .
Starting in the late 1900s, robber barons and socialites established summer “cottages” in the area, ranging from stone Victorian homes to sprawling manor houses with acres of grounds. Many of these homes have found a second life as spa resorts or hotels, adding grandeur to the season of art and music that fills the hills each summer.
The Southern Berkshires are easily accessible from the Mass Pike (I-90) and Route 7. Bonanza Bus Lines (888/751-8800, www.peterpanbus.com ) runs buses to the region. In Lenox , they stop at Village Pharmacy (5 Walker St.); in Stockbridge , at the visitor booth on Main Street, and in Great Barrington , at the visitors center at 362 Main Street. Peter Pan Bus Lines (800/343-9999, www.peterpanbus.com ) also runs buses to the Village Pharmacy in Lenox.
Buses throughout the region are run by the Berkshire Regional Transit Authority (413/449-2782 or 800/292-2782, www.berkshirerta.com ).