Main Street looks much the same as when his painting was completed in December 1967, 11 years after he started it, and published in McCall's Magazine.
Rockwell described the second-oldest community in Berkshire County (after Sheffield) as "the best of America, the best of New England."
Filled with historic houses, cultural attractions such as Tanglewood, the Norman Rockwell Museum, Naumkeag, the Mission House and Chesterwood, one of the county's most beautiful lakes, the 234-year-old Red Lion Inn, the high-end Wheatleigh resort, the Kripalu new-age spa, numerous B&Bs and the highly regarded Berkshire Country Day School, it has become part resort town, part vacation retreat for prosperous urbanites. But it retains a down-to-earth, homegrown spirit and a tradition of close community spirit handed down from previous generations to current natives and long-time residents.
The Laurel Hill Association, the nation's oldest village improvement society, helps to carefully protect the town's unspoiled appearance; there are no traffic lights or fast-food joints.
Visitors flock to the town to experience the nostalgia of a tranquil way of life that's hard to find elsewhere. The quintessential small-town New England atmosphere at its best can still be found, despite the enroachment of development and sprawl in adjoining communities up and down Route 7. The only drawback is the traffic-choked town center on summer weekends and, increasingly, weekdays, too. Also, with the exception of basics available at the Elm Street Market, shopping must be done in Lee, Great Barrington or other communities.
With the second-highest property values in the county (behind Alford), the county's highest percentage of second-home owners, and one of the highest household income levels, town officials have kept the budget under careful management, resulting in one of the county's lower property tax rates, $6.85 per $1,000 of assessed value. According to Mike Blay, the town's principal assessor, nearly two out of three homes are owned by seasonal residents. The number of year-round permanent residents has declined by about 18 percent in the past seven years, according to federal and town census reports.
Settled in 1734 and incorporated five years later, Stockbridge had been called Wnahtukook, the Great Meadow, by the Mahican Indians. The Massachusetts General Court (state Legislature) gave the area to the Indians as a grant, and it became known briefly as Indian Town.
Two of the first white settlers, missionary John Sergeant, considered the founder of Stockbridge, and teacher Timothy Woodbridge, worked together with the Indians while seeking to convert them to Christianity.
Several Indians including Konkapot, the chief, and Umpachene served as selectmen along with the whites; Mahicans also fought as rangers in the Revolutionary War. Early settlers clustered around the mission church in the center of Stockbridge; later arrivals formed outlying neighborhoods that became the villages of Interlaken and Glendale (which still has its own post office). While Sergeant and Woodbridge lived among the Indians near the Mission House, other white settlers including Ephraim Williams of Newton, Josiah Jones of Weston and Ephraim Brown of Watertown arrived in 1737 and congregated on Prospect Hill, aloof from the tribe.
But Indian Town thrived as the native Americans tripled their crop and money flowed in from Governor Jonathan Belcher and supporters of the missionary enterprise in London. To keep the contributions flowing, the town was incorporated in 1739 and named for the town in Hampshire County, England.
After Sergeant's death in 1749, the fortunes of the Indians began a precipitous decline. In 1785, their land having been sold, the impoverished tribe was guided by Sergeant's son to Oneida County, New York, where they named their community New Stockbridge. In 1833, they and the Oneida Indians migrated to Green Bay, Wis., where they joined with the Munsee tribe and in 1850 relocated yet again to a reservation near Shawano. Descendants are still known as the Stockbridge Indians.
The Native Americans who first settled in Stockbridge are commemorated at the Mission House, a museum operated by the Trustees of Reservations and open to the public, and by a monument overlooking the golf course. Several are buried in a corner of the Stockbridge Cemetery.
In 1773, the Red Lion Inn, originally known as the Stockbridge House, was established in the center of town by Anna and Silas Bingham, first as a general store and then as a stagecoach stop and gathering place for villagers and visitors. It was part of the headquarters for the 1786 tax revolt known as Shay's Rebellion. Nearly destroyed by fire in 1896, it was restored and reopened in time for the 1897 summer season. The inn was closed during the 1950s and nearly fell victim to the wrecker's ball in 1968; a gas station was slated to replace it.
But business entrepreneur Jack Fitzpatrick and his wife Jane saved it, turning it into the grande dame of area resorts, opening it year-round for the first time, and establishing their Country Curtains business there (soon, it outgrew the space and relocated several miles to the east). Fitzpatrick served four terms as Berkshire state senator; the Fitzpatricks are the county's greatest arts supporters and philanthropists.
The inn, greatly expanded, is now owned by their daughter Nancy and remains a leading dining and lodging destination.
According to historical accounts, the community in the late 1700s and well into the 1800s was disheveled, with dusty, weedy streets and decrepit fences that allowed livestock to roam freely. By 1853, the Laurel Hill Association was formed by Mary Hopkins, a great-grandaughter of John Sergeant, to help beautify the community; it continues to maintain parks, wooded areas and hiking trails today.
The arrival of the railroad in 1850 spurred the community's development as a summer destination for wealthy New Yorkers, along with Lenox, as the Gilded Age flowered and then withered in the early 1900s. Led by Theodore Sedgwick, a lawyer, politician and statesman, and his daughter Catharine M. Sedgwick, the nation's first famed female author, the town gained a reputation as a mecca for writers and artists a tradition that still is going strong.
Elizabeth "Mum Bett" Freeman of Sheffield, who gained her freedom as part of the successful 1781 lawsuit that declared slavery unconstitutional in Massachusetts, lived the rest of her life in Stockbridge, working in the Sedgwick home. She is buried in the "Sedgwick Pie" section of the town cemetery. (Among her great-grandchildren was W.E.B. Du Bois, the civil-rights leader and author who lived in Great Barrington.)
In 1928, the Stockbridge Casino was relocated and converted into the Berkshire Playhouse, later renamed as the Berkshire Theatre Festival it's the oldest, continously operated performing-arts institution in the county. Later, the Norman Rockwell Museum first at the Old Corner House in the center of town and later expanded at a new location in Glendale helped attract visitors, as did the former residence and studio of sculptur Daniel Chester French and the former Choate residence named Naumkeag.
The Tanglewood summer music festival and institute for promising young musicians was created by Boston Symphony Orchestra Music Director Serge Koussevitzky in 1937 on the Tappan estate following modest beginnings a year earlier on the Holmwood estate (now Foxhollow, on the Lenox-Lee line). (The New York Philharmonic performed in the summers of 1934 and 1935 on the Bonnie Brier farm in Stockbridge). Nearly all of the BSO's property today lies within Stockbridge, except for the Main Gate box office and adjacent the parking areas along West Street in Lenox. The area had been named by Nathaniel Hawthorne, whose "Tanglewood Tales" was written in a small cottage he had rented from the Tappans in 1850.
After he departed, the Tappans retained the name for the cottage (a replica still stands today) and their estate overlooking Stockbridge Bowl.
Mary V. Flynn has been described by author Dan Valenti as "the heart and soul of Stockbridge" she calls it "the nicest compliment I've gotten." Declaring that she stands "second to none in my love for the town," Flynn, now 87, has lived in the same Shamrock Street house since she came home from the hospital when she was nine days old. She taught in the Dalton school system for 36 years, starting in 1943, served for 15 years on the Select Board (1978-1993) and describes herself as an "active worker for the Democratic party" since she was 12. She was director of the Chesterwood Museum during the 1960s.
She declares her "strong affection for the town where I have one foot in time and one foot in eternity. I was fortunate to be brought up in this beautiful place. We had a very close community spirit, and I always try to keep that kind of community spirit because you see it so rapidly disappearing."
Flynn's Stockbridge roots go back to 1857; her father was born in that year in a nearby house on Vine Street. Never married, she quips that "my mother used to say no man would put up with me, he would send me packing in two weeks." She reports that she had a "terrible time" getting through college because she missed the town so much; even now, on vacation, she quickly becomes homesick. Since her mother died in 1971, she has lived alone in her house.
Flynn recalls that when she was young, "it was not a tourist town. Everything you needed in life you could buy in Stockbridge we had a tailor shop, a cobbler shop, two drug stores, two meat markets, a fish market, a dry goods store, even a jewelry store." Now, she observes, "you can't buy a needle or a nail in Stockbridge. Tourism became an economic reality, that had to happen. The little stores, the community stores couldn't compete with the way business is conducted today. We moved into serving a community of tourists and visitors. I always felt we should greet them, because when I go somewhere, I like to be greeted.
"I hate to see great big houses going up, replacing small houses that were preserved as part of the village. I like to see older things preserved because we lose the ambiance of the town if we lose them," Flynn declares. "You can't stand in the way of what people call progress, but I don't call it progress. I believe in moderation in all things you have to go along with some of the new things but you shouldn't give up all the old things."
Retaining the Rockwellian image of the town is among the Select Board's major concerns, according to Chairman George Shippey.
"We don't want to lose the mystique captured by Rockwell," he says, vowing that the town will never harbor traffic lights, fast-food chains or malls. "But the downside is that you have to go out of town to get prescriptions or hardware."
Shippey acknowledges that Stockbridge "is not that receptive to change." He recalls the flap that ensued several years ago when a third stop sign was erected at the congested intersection of Main and South streets to ease the flow of traffic.
Second-home owners are "the industry for Stockbridge," he points out. "They're here for the cultural events, but they don't have children in the school system and they hardly get any services from the town."
Shippey maintains that the Select Board is attuned to the seasonal residents' concerns, citing their annual meeting with the Selectmen on the second Saturday in July.
"All in all, it's a very good relationship," he concludes. "There's no animosity, as there is in some communities."
Shippey hopes the town's population decline can be stabilized or reversed as more seasonal homes are renovated for year-round use around Stockbridge Bowl.
He calls the aging of the town's population "a little distressing; we need to see more young people in Stockbridge," though the high price of property is a major barrier. Shippey notes approvingly the affordable-housing development, Pine Hills, managed by Construct Inc.
"There are a lot of young families there with children, it's nice to see," he says.
Through the efforts of the Stockbridge Bowl Association, the infestation of the milfoil weed is under attack through more substantial winter drawdowns and the day-to-day efforts of two town-owned weed harvesters. The war on weeds will be intensified by a diversionary pipe adjacent to the gas line and sewer line in the outlet section of one of the state's most-prominent lakes; in the future, selective dredging during the winter months is on the drawing boards.
Shippey is optimistic about the development of an equestrian resort on the scenic Route 183 property of the defunct De Sisto School, formerly the Stockbridge School headed by Hans Maeder and, before that, the Bonnie Brier Farm.
"This will be a wonderful project for the use of that property and a great fit for Stockbridge and Berkshire County," he said, predicting the town permitting process will proceed without a hitch.
Mystery still shrouds the intentions of the Delancey Street Foundation, owner since 2002 of the large white house at 8 South St., former home of Norman Rockwell. The San Francisco-based organization offers residential rehabilitation for former addicts, ex-convicts and others who have been "down on their luck."
According to the foundation's Web site, once renovations to the Stockbridge property are completed, "Delancey Street will utilize this home for training residents who have completed their two-year commitment who will get the opportunity to study there to develop their talents in the arts."
Plans for the site are the topic of much conjecture in town; Shippey hopes foundation representatives will meet with the Select Board soon, noting that the property has been well-maintained and property tax payments are up-to-date.
"We need to sit down with them," he said. "We have a lot of questions, we don't have the answers, that's where we're at."
Depending on the foundation's plans, Shippey speculates that a special-permit application may be required from the Planning Board.
Town officials are eagerly awaiting their early September relocation from offices in Procter Hall on West Main Street to the renovated Stockbridge Town Office at the former Stockbridge Plain School. The second floor is being rented to tenants, including the Berkshire Hills Regional School District for administrative offices; Shippey anticipates that the Stockbridge Chamber of Commerce and a local physician will be among the tenants.
"It's going to be a wonderful community building," he enthused it will include a "very large senior center," new headquarters for the police department, and a home for local athletic programs in the gymnasium. The town is repaying a long-term $6.9 million bond, but Shippey anticipates no increase in the tax rate will be needed to service the debt. Procter Hall will be restored as a meeting house and a space available for rentals.
A recent sewer-extension project in Glendale and parts of the Stockbridge Bowl area having been completed recently, the only capital project Shippey anticipates is a new water tower on Eden Hill, site of the Congregation of Marians, to ease low water-pressure problems in the center of town caused by aging pipes.
As octogenarian Mary Flynn puts it, "Stockbridge has managed to the present to keep an inner integrity. ... People have been so nice. Stockbridge is the most wonderful community to live in and grow old in. I wouldn't change it for anything in the world."