The best months to visit the Berkshires are May to October. Music and theater fans will want to aim for July and August to take advantage of the various summer festivals. Leaf watchers should plan tours through the countryside in late September or early October. For visitors who prefer to avoid the tourist season, I would especially recommend May or June and the week or two after Labor Day.
Start by calling the Berkshire Visitors Bureau (1-800-BERKSHR) for a copy of their summer guide. Published every year about April 1, it contains theater, music, and dance schedules, hotel and restaurant listings, hours for museums and houses, et cetera. While waiting for it to arrive, hunt up a copy of The Berkshire Book (1986), by Jonathan Sternfield. It offers a complete guide to history, culture, hotels, and shopping in the area. The restaurant reviews are especially useful—outspoken and on target.
For those who want to cover all of the Berkshires, and there are many places of interest both west and east of those mentioned here, it would be best to travel by car and stay in a different hotel each night, being sure to try at least one of the small inns like the Williamsville Inn or the Hancock Inn (in Williamsville and Hancock, respectively). Travelers who prefer to have a home base from which to make day trips will find the best selection of comfortable and historic hotels in Lenox, including the Birchwood Inn (about 1840), the Village Inn (1771), and the Gateways Inn (1902). Also, a couple of mansions have been converted into luxury accommodations, among them Blantyre, a summer cottage built in 1902, and Wheatleigh, an 1893 copy of a sixteenth-century Italian palazzo.
Recommended reading: Berkshire, The First Three Hundred Years, 1676–1976 , put out by the Eagle Publishing Co.; The Berkshire Cottages: A Vanishing Era, by Carole Owens; and Literary Life in Nineteenth-Century Berkshire County, by Luther Stearns Mansfield, published by the Berkshire County Historical Society.