Autumn is the peak season for the Berkshires — foliage colour peaks in mid-October and the combination of crisp weather, golden hills, and open cultural attractions draws large crowds from New York and Boston. Accommodation prices peak accordingly and should be booked weeks in advance for October weekends.
Summer is the other major season: Tanglewood (the Boston Symphony's summer home in nearby Lenox) runs from July through August, and the surrounding cultural institutions are fully open. Winter is quiet and many attractions reduce hours or close entirely; the landscape is beautiful under snow but the village feels emptily peaceful. Spring is the most underrated time: the crowds are gone, prices are reasonable, and the Berkshires hills green up quickly after April.