Sandisfield — It was the biggest news story to hit Sandisfield in years, perhaps since the Congregational church fire of 1908. Despite being the least densely populated town in Massachusetts, the story reverberated through this sprawling Berkshire County town of 900 at the speed of semireliable internet. Hours after the accident, the Sandisfield Times, a relatively new local paper with an unusual provenance, quickly emailed out a breathy “extra” edition to resident subscribers.
Sandisfield’s centuries-old New Boston Store was half demolished by a runaway asphalt truck on a Tuesday in a spectacular early-morning crash — a brake-failure accident that authorities said could have been much, much worse, read the lede.
Curiously, the truck-vs.-general-store news story wasn’t altogether surprising. Perched beside a narrow bridge along a precariously tight turn that comes off a steep hill, the store, believed to be one of the longest continuously running stores in America, had been hit before — countless times.

What was surprising was the byline: Simon Winchester. Yes, that Simon Winchester. The widely admired best-selling nonfiction author. The guy with “OBE” at the end of his name — as in “Officer of the Order of the British Empire,” an award presented by the Queen of England herself, and mere notches from knighthood.
“I was quite nervous at first,” said Winchester, 73, the author of 30 books, including the best-selling “The Professor and the Madman.” “But I managed to find my footing. Before I knew it, it was like the old days at the Guardian,” where Winchester worked in the 1970s.
Winchester isn’t just an occasional reporter for the small-town monthly with a circulation of 1,000 and a $12,000 annual budget — he’s its founding editor. “I wanted to create a sense of community in a town that has no downtown or sense of cohesion given that it’s spread out over 53 square miles,” said Winchester. “And I believe the paper has done that to a certain degree.”

A half-mile from Winchester’s farm, there’s a lonely historical marker that pretty well sums up Sandisfield’s rural charm, as well as its frustrating lack of community structures. The plaque states that this is where the town center once stood — a place of taverns, stores, shops, a thriving farmer’s market and a Congregational church. After centuries of slow depopulation, all that remains is a rutted grassy field imbued with nostalgia.
There’s no polite way around it: Sandisfield is in the boonies, the sort of place residents love for its remoteness — vast tracts of land, dense woods and the ability to hear a moose braying in your backyard. I live in neighboring Great Barrington but, as I approached Winchester’s homestead for an interview and tea, I could’t help asking myself: Where am I? Then the dirt road turns to mud. Then I’m lost.
When I eventually turned onto Winchester’s handsome property, I was greeted by a smiling Setsuko, Simon’s wife, an artist and former NPR producer. I was quickly distracted by a loud and oddly throttled honking noise in the distance. “Oh, that’s just Goosie,” Setsuko explained — the family goose. I looked out over an old-growth apple orchard, which the Winchesters use for making cider, and saw a chicken run in the distance. “Goosie protects the chickens from fisher cats,” Setsuko explained.

I could’t help but admire their immaculately restored home. Parts of it are older than the town itself, which was settled in 1750 and incorporated in 1762. It’s clear from the objects scattered about — a high-powered telescope, elaborate antique barometers, grandfather clocks and a gorgeous AGA hearth stove — that this is the home of a curious mind drawn to traditional instruments, particularly of scientific inquiry. “Simon loves his barometers,” Setsuko said. “And there are clocks everywhere. He’s always winding them.”
Simon waited for me in his writing studio, an immaculately restored stand-alone structure that he alternately refers to as his study, library and, half-jokingly, as his scriptorium. It’s an enviously peaceful writing sanctuary — a warm, orderly space filled with shelves upon shelves of books and endless drawers of maps. It was here, eight years ago, while finishing up “Atlantic,” his biography of the ocean and beginning research for “The Men Who United the States,” that Winchester wrote and edited the first issues of the Sandisfield Times.

“I’m a fan of remote places,” said Winchester, a self-described voluntary hayseed who recently bartered his old laptop for half a pig. “I like quiet. And this is so quiet. There’s nothing here, nothing at all. It’s half-hour each way for a stick of butter or a quart of milk.”
Indeed, as the historical marker makes abundantly clear, there aren’t a lot of places in Sandisfield for residents to meet. They used to run into one another at the general store — until the asphalt truck ran into it. There’s a small post office, but its hours have been reduced and residents fear its days are numbered. The schools are already gone, now located in neighboring communities. The town dump is pretty much the only public space residents run into one another.
Winchester was determined to provide his adopted community with a better way to exchange information than serendipitous chatter at the dump. One bitterly cold January night over dinner with friends, a time of year when one is particularly thankful to see neighbors, Winchester hatched the idea of a community newspaper. “A well-written newspaper that the community could be proud of could change everything,” he decided. The other guests, residents themselves, agreed.
Growing up in a one-pub town of 1,000 in southwest England, Winchester developed a soft spot for community. A great admirer of American democracy — he became a U.S. citizen in 2011 — and particularly passionate about the New England town-meeting form of government, he had big goals for the publication from the start. “The democracy in New England is the purest form one can have,” Winchester says. “But people need to be informed and government needs to be held accountable.”
The masthead would have to be impressive, worthy of the community it represented, with an old-time crest, like the Times of London, “to make it look classical,” with “proper typeface,” and a motto in Latin to add additional gravitas. Winchester found an older version of the Massachusetts state crest that he liked, chose Tribunus Plebis (“Guardian of the People”) as the motto and added the newspaper’s mission to the masthead as well: “Reliable. Regular. Relevant.”
A few months and several editorial meetings later (comprised solely of volunteers), the first issue hit the streets April 1, 2010. A product of British journalism, Winchester came out guns blazing on a particularly burning local issue: Decades after being condemned as blight, two empty houses remained eyesores along an entrance to the community. The headline spanned the top of the entire front page: “Route 8 Houses: A Solution at Last?”

As a former small-town selectman myself, I’ve learned that there’s a quiet satisfaction in getting things done on the local level — new streetlights, a ban on plastic bags, a thoughtful budget. Winchester’s avenue became his newspaper. Coverage of the blight stirred the community to action. The decrepit homes became a hot issue that the town selectmen soon addressed, and which the community then voted to demolish. The properties were torn down that same year, their destruction joyfully recounted in the newspaper in blow-by-blow photo collages. Winchester was clearly pleased by the power of the press when applied to his own community. “There were some immediate successes,” he said with an earnest nod.
To Winchester’s chagrin, not everyone wanted to be informed, at least not by an outsider. With his refined British English, aggressive tone (to locals at least) and second address in Manhattan, Winchester was a perfect combination of what many locals dread: the hoity-toity know-it-all New Yorker with a fancy second home in the woods. The last thing they wanted to read were the opinions of nonlocals intervening in their multigenerational town affairs. Suffering through their alleged arrogance and strange ways each summer when the town’s population swelled to 2,500, locals smarted at how, instead of hunting deer, these part-time residents hunted for antiques and cultural offerings.
Ironically, Winchester’s outsider status helped him establish an historical connection to Sandisfield that few, if any, in town could similarly claim. When living on an island in the Hebrides, he became quite friendly with the descendents of Lord Sandys, the town’s colonial treasurer, who, until the revolution, paid the community’s bills from London.
“At first, people hated it,” Winchester admits, adding that, at the Memorial Day parade that year, there was a float with someone sitting atop a toilet reading his newspaper. “The paper was initially seen as a way of dividing the community between the well-off New Yorkers and the locals. It was doing just what I didn’t want it to do.”
To Winchester’s credit, he pressed ahead with the newspaper, writing many of the articles himself that first year. The paper covered town elections, discussing issues and profiling candidates in a way that would otherwise have never happened. If it were not for the Times’ candidate roundup, many residents might not have known who was running, and for what office, until they reached the voting booth. Additionally, Town Hall employees were re-introduced to the community in the form of featured profiles, as were local businesses. The board of selectmen got their own column to update the public on town business.

Winchester and his editorial board drafted volunteers to write columns about beekeeping, gardening, birds, elder activities, stargazing and cooking. There were features on local swimming holes, bear sightings and musings from the town dump employee. There was also hard news of real importance to the community, including a proposed Kinder Morgan gas pipeline extension through protected land and the frustratingly slow arrival of broadband Internet.
Opinion soon swung in the paper’s favor with locals embracing Winchester’s creation as a legitimate and convenient means of communication. “People feared it was going to be very snobby at first,” said Margaret O’Clair, a board of health volunteer. “But now everybody reads it. It’s a quality paper — it doesn’t smudge like others do. And quality journalism, too.”
O’Clair was a contributor to the paper in its earlier years. “I used to write a column about local birds,” she said. “It ran for about two years. And then I ran out of birds.” The lede to one of her early columns summed up the initial mood in town. “Not all our summer visitors come up from Manhattan,” she wrote. “Members of the warbler family travel much further …”
Recognizing that his English wit wasn’t always translating well locally, Winchester began to soften his tone a touch. The lighthearted “Hatched, Matched, and Dispatched” soon became “Comings and Goings,” and articles felt more cooperative in spirit than confrontational.
But Winchester’s mischievous side continued to emerge from time to time. On the newspaper’s first anniversary, which fell on April Fools’ Day, Winchester chronicled the sighting of a griffin in town woods by none other than bird columnist O’Clair, who was described as tossing back hearty nips of whiskey at the time. The mythical creature’s screech was described as akin to the pronunciation of a local family’s unusual name. Bird columnist and local family-with-distinctive-name were none too amused.
And perhaps Winchester had a bit more fun than he maybe should have covering the fate of Jellybean, a cat said to be shot by a neighbor with a BB gun after said cat was allegedly caught harassing chickens. The state police were summoned to investigate. “I absolutely could not turn down a story about the shooting of a cat named Jellybean,” said Winchester, “even if it was only an alleged shooting.” Winchester’s journalism instincts were justified: Jellybean was indeed shot, although not seriously. The kitty with the candy name recovered fully, with as many as eight lives still intact.
Winchester recounted the story over afternoon tea together — Earl Grey and a generous spread of biscuits and fine cheeses. “I wanted to rigorously cover Sandisfield and only Sandisfield, not the surrounding communities and their cultural events,” Winchester said between bites. “There was this feeling among some that there wouldn’t be enough news here to fill a paper. But as a newspaperman for 31 years, I know that, behind every front door, there’s a story. I remain convinced of that to this day.”

Through trial and error, Winchester learned that one generally has to be “a bit more kind and gentle” when writing about neighbors in a very small community. It helps, for example, to either know the people you’re lampooning, or to at least give them a heads-up. Other lessons were less cheeky and remain painful to discuss. Early on, the paper came out against a candidate for the board of selectmen. In what felt like a victory for good journalism and good government, the man lost the election. Then, in the following months, his baby died from a long illness, followed by his heartbroken wife.
Now in its eighth year, the Sandisfield Times has a proven track record of informing its readers on topics of importance while bringing a new vitality to the democratic process. Attendance at board of selectmen meetings has surged, as has attendance at the annual town meetings, at which residents discuss and vote on the budget (currently $3 million) and proposed bylaws.
“The newspaper has been an incredible resource for the community— a real game-changer,” said Selectman Alice Boyd. “A paper has the ability to flush out a story and get the facts out. It gives us an avenue to talk about issues publicly in a way that everyone becomes better informed. It has absolutely changed our community for the better. It’s brought people here together in a big way.”
Winchester has stepped back from the running of the paper but continues to write columns and the occasional story about school budget debates, the sort of story usually covered by a cub reporter but which Winchester performs with genuine interest. He’s passed off the voluntary editorial duties, first to Setsuko and then to Bill Price, another retired journalist. “Simon’s a very facile writer, and always keeps his deadlines,” Price said of editing Winchester. “The Times’ readers are getting the real Simon Winchester: witty, strong and pointed.”
Even more remarkable to Price is that the little monthly still exists. “Normally a paper like this would run out of steam,” he said. “Eight years later, we’re still chugging along.” Volunteers keep volunteering, advertisers keep advertising and, despite fears to the contrary, the paper hasn’t run out of stories to tell.
Under Price’s leadership, the paper has also managed to heal the rift between locals and second-homeowners, with both groups feeling like they have a voice. It helps that the paper runs a lot of soft features (“Black Flies? No Like-ums”) and covers most news stories with the assumption that people who step up to serve in small-town government have good intentions and are doing their best. “A paper that’s too aggressive can drive people apart, maybe unnecessarily,” said Price.
As the seasons change and years come and go, Sandisfield continues to be an economic backwater beloved by its residents yet wrestling with issues that matter. Broadband Internet — a critical rural lifeline in today’s world — remains tantalizing close, yet just out of reach. The town has lost its battle against the gas pipeline, which crosses Sandisfield but doesn’t serve it. And the old general store is no more.
It took a demoralizing two years for the asphalt truck to be removed from the interior of what was Sandisfield’s hub. The truck was left to support the second floor as lawyers and insurance companies squabbled. Last year the little store that continuously ran since 1790 was demolished all together, its destruction covered in mournful contrast to Winchester’s campaign against the blighted homes.
Nevertheless, this community of 900 important souls still has a newspaper, one that informs and communicates with its readers, who, despite being scattered across 53 square miles, continue to feel connected to one another.
“The Sandisfield Times,” said Price, “is acting as the town center.”