Sheffield: 119 miles N of New York City and 143 miles W of Boston; Great Barrington: 6 miles N of Sheffield; Stockbridge: 8 miles N of Great Barrington; Lee: 4 miles NE of Stockbridge; Lenox: 6 miles north of Stockbridge; Pittsfield: 7 miles north of Lenox; Williamstown and North Adams: 21 miles N of Pittsfield, 202 miles N of New York City, and 131 miles NW of Boston.
More than hills but less than mountains, the Taconic and Hoosac ranges that define this region at the western end of Massachusetts go by the collective name "The Berkshires." The hamlets, villages, and two small cities have long drawn sustenance from the region's kindly Housatonic River and its tranquil tributaries, and are as New England as can be.
Mohawks and Mohegans lived and hunted here, and while white missionaries established settlements at Stockbridge and elsewhere in an attempt to Christianize the native tribes, the Indians eventually moved west. Farmers, drawn to the narrow but fertile flood plains of the Housatonic, were increasingly supplanted in the 19th century by manufacturers, who erected the brick mills that drew their power from the river.
At the same time, artists and writers were attracted by the mild summers and seclusion that these hills and lakes offered. Nathaniel Hawthorne, Herman Melville, and Edith Wharton were among those who put down temporary roots. By the late 19th century and the arrival of the railroad, wealthy New Yorkers and Bostonians had discovered the region and begun to erect extravagant summer "cottages." With their support, culture and the performing arts found a hospitable reception. By the 1930s, theater, dance, and music performances had established themselves as regular summer fixtures. Tanglewood, Jacob's Pillow, and the Berkshire and Williamstown Theatre festivals draw tens of thousands of visitors every summer.
Note that many inns routinely stipulate minimum 2- or 3-night stays in summer and over holiday weekends, and often require advance deposits.