The first settlement of any size encountered when approaching from Connecticut on Route 7, Sheffield occupies a flood plain beside the Housatonic River, 11 miles south of Great Barrington, with the Berkshires rising to the west.

Agriculture has long been the principal occupation of its residents and still is, to a degree. Everyone else sells antiques, or so it might seem driving along Route 7 (also known as Main St. or Sheffield Plain). The meticulously maintained houses cultivate an impression of prosperous tranquillity.

Memorial Day to Columbus Day, stop by the Ashley House, Cooper Hill Road, in Ashley Falls (tel. 413/298-3239; Built by Colonel Ashley himself in 1735, this modified saltbox is believed to be the oldest house in Berkshire County. Ashley was a person of considerable repute in Colonial western Massachusetts: a pioneer settler, an officer during one of the French and Indian Wars, and later a lawyer and a judge. The house is open from 10am to 5pm on Saturday and Sunday. Admission to the grounds is free; tours of the house are $5 for adults and $3 for children 6 to 12. To find it, drive south from Sheffield on Route 7, then veer onto Route 7A toward Ashley Falls. Bear right on Rannapo Road. At the Y intersection, turn right on Cooper Hill Road.

South Egremont

If you're coming to the Berkshires from the Taconic Parkway in New York, you can't help but drive through the town of Egremont. Its larger, busier half is South Egremont, once a stop on the stagecoach route between Hartford and Albany. It retains many structures from that era, including mills that utilized the stream that still rushes by. Those circumstances make it a magnet for antiques dealers and restaurateurs.

Great Barrington

Even with a population barely over 7,500, this pleasant retail center, 7 miles south of Stockbridge, is the largest town in the southern part of the county. Rapids in the Housatonic provided power for a number of mills in centuries past, most of which are now gone, and in 1886 this was one of the first communities in the world to have electricity on its streets and in its homes.

Great Barrington has no sights of particular significance, leaving time to browse its many antiques galleries and specialty shops. Convenient as a home base for excursions to such nearby attractions as Monument Mountain, Bash-Bish Falls, Butternut Basin, Tanglewood concerts, and the historic houses of Stockbridge, it has a number of unremarkable but entirely adequate motels north of the center along or near Route 7 that tend to fill up more slowly on weekends than the better-known inns in the area. Great Barrington is something of a dining destination, too, with 55 eating places, including, at last count, four sushi bars!

A farmer's market is held on Saturday from 9am to 1pm in season at the train station on Castle Street.

The Southern Berkshire Chamber of Commerce maintains an information booth at 362 Main St. (tel. 413/528-1510;, near the town hall. It's open Tuesday through Sunday from 10am to 5pm.


Stockbridge's ready accessibility from Boston and New York (about 2 1/2 hr. from each and reachable by rail since the mid-19th century) transformed the original frontier settlement into a Gilded Age summer retreat for the rich. The town has long been popular with artists and writers as well. Illustrator Norman Rockwell, who lived here for 25 years, rendered the Main Street of his adopted town in a famous painting. Along and near Main Street are a number of historic homes and other attractions, enough to fill up a long weekend, even without the Tanglewood concert season in nearby Lenox. One of the Berkshires' hottest destinations, Stockbridge is inevitably jammed on warm weekends and during foliage season. A prominent event is the Christmas celebration on the first Sunday in December, when over 50 antique cars are parked along Main Street to help re-create the scene painted by Norman Rockwell decades ago.

Stockbridge lies 7 miles north of Great Barrington and 6 miles south of Lenox. The Stockbridge Chamber of Commerce (tel. 413/298-5200; maintains an information booth opposite the row of stores depicted by Rockwell. It's open May through October.


While Stockbridge and Lenox were developing into luxurious recreational centers for the upper crust of Boston and New York, Lee was a thriving paper-mill town. That meant that it was shunned by the wealthy summer people and thus remained essentially a blue-collar town of workers and merchants. It has a somewhat raffish though not unappealing aspect, its center bunched with shops and offices and few of the stately homes that characterize neighboring communities.

The area's contribution to the Berkshire cultural calendar is Jacob's Pillow Dance Festival in Becket, which first thrived as "Denishawn," a fabled alliance between founders Ruth St. Denis and Ted Shawn.

Lee is 5 miles southeast of Lenox. In summer and early fall, the Lee Chamber of Commerce (tel. 413/243-0852; operates an information center on the town common, Route 20 (tel. 413/243-4929). It can help you find lodging, often in guesthouses and B&Bs -- rarely as grand as those in neighboring Lenox, but nearly always cheaper. That's something to remember when every other place near Tanglewood is either booked or quoting prices of $300 a night.

Lenox & Tanglewood

Stately homes and fabulous mansions mushroomed in this former agricultural settlement from the 1890s until 1913, when the 16th Amendment, authorizing income taxes, put a severe crimp in that impulse. But Lenox remains a repository of extravagant domestic architecture surpassed only in such fabled resorts of the wealthy as Newport and Palm Beach. And because many of the cottages have been converted into inns and hotels, it is possible to get inside some of these beautiful buildings, if only for a cocktail or a meal.

The reason for so many lodgings in a town with a population of barely 5,000 is Tanglewood, a nearby estate where a series of concerts by the Boston Symphony Orchestra is held every summer.

Lenox lies 7 miles south of Pittsfield. The Lenox Chamber of Commerce (tel. 413/637-3646; provides visitor information and lodging referrals.


Berkshire County's largest city (pop. 45,793) routinely gets little attention in most tourist literature. A commercial and industrial center, it has little of the charm that marks such popular destinations as Stockbridge and Lenox. Something is afoot, though. Always a convenient base for day excursions to other parts of the central Berkshires, this blue-collar city is reinventing itself, with new attractions, more worthwhile restaurants, and an ever livelier nightlife. Emblematic of this shift was the recent reopening of the 1903 Colonial Theatre, once again home to over 200 nights per year of dance, comedy, and music from classical to country.

A recently discovered document banned the playing of baseball within 80 yards of the main church in 1791, giving Pittsfield claim to the invention of the game, 48 years before Cooperstown, New York. In summer, the Berkshire Black Bears (tel. 413/448-2255) play minor-league baseball at Wahconah Park, a 1919 stadium with real wooden box seats.

The Berkshire Visitors Bureau (tel. 800/237-5747 or 413/443-9186; is in the same block of buildings as the Crowne Plaza Hotel, on Berkshire Common.


This community and its prestigious liberal-arts college were both named for Col. Ephraim Williams, who was killed in 1755 in one of the French and Indian Wars. He bequeathed the land for creation of a school and a town. His college grew, spreading east from the central common along both sides of Main Street (Rte. 2). Over the town's long history, buildings have been erected in several styles of the times. That makes Main Street a virtual museum of institutional architecture, with representatives of the Georgian, Federal, Gothic Revival, Romanesque, and Victorian styles (and a few yet to be labeled). Inserted into this diverting display is the '62 Center for Theatre and Dance, a thoroughly contemporary structure that opened in September 2005. It stands at dignified distances from the older buildings, so what might have been a tumultuous visual hodgepodge is instead a stately lesson in historical design. The impressive Clark Art Institute is the best reason to make a special trip, perhaps in conjunction with a performance at the increasingly ambitious Williamstown Theatre Festival.

A free weekly newspaper, the Advocate (, produces useful guides to both the northern and southern Berkshires. An information booth, at North Street (Rte. 7) and Main Street (Rte. 2), has an abundance of pamphlets and brochures free for the taking.

North Adams

In the mid-1990s it seemed impossible that this comatose mill town could recover. Its unemployment rate was the highest in the state, and over two-thirds of its storefronts were empty. A land developer once even suggested that the town be flooded to create lakefront property.

However, North Adams experienced a whiplash turnaround, and today many of those once-abandoned storefronts are taken up with restaurants, galleries, and high-tech start-ups. The unlikely reason, to almost everyone's agreement, is an art museum that opened in 1999. An abandoned industrial complex has been converted, despite early hoots of derision, into a center for the visual and performing arts. It is called the Massachusetts Museum of Contemporary Art, and it has strikingly altered the socioeconomic dynamic of North Adams.

The first Sunday of October is Fall Foliage Day, with a parade of fire engines, marching bands, and Clydesdales, and balloons, hot dogs, and cotton candy on sale at sidewalk stands.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.