Filmmaker Philip Milano of Dover Plains holds the Scotch U-matic cassette containing his original 1970s documentary about the Harlem Valley Transportation Association.
Philip Milano, the filmmaker and longtime Dover Plains resident, made the film as a student project during his time at New York University.
“It took me about a month to make,” Milano said. “I played all the music myself, lined up the interviews and edited it.”
The 28-minute film chronicles the efforts to retain passenger and freight rail service between New York City and Chatham, New York in the 1960s and 1970s.
Milano was contacted last year by a former Copake Falls resident who wanted to view the film for research. Skeptical that the old Scotch U-matic cassette – a bulky, professional-grade videotape used in the 1970s – would still play, Milano agreed to ship the only existing copy of his movie out west. To his surprise, it was successfully digitized.
Aly Morrissey
The video is slightly grainy with crisp audio. Footage shows the former Saperstein’s building – now Westerlind – and its famed railroad mural, along with shots of the old Sharon and Millerton stations.
In an early scene, a young Holly Nelson – co-founder of Oblong Books – stands in her store and speaks passionately about the loss of rail service and its impact on rural businesses, farms and residents.
“It brings in the whole question of rural powerlessness,” Nelson said, warning that locals would soon become “highway hostages,” forced to drive gas-guzzling cars.
The late Frank Perotti, who served as the supervisor of North East for more than a decade, also appears, speaking about the loss of freight service affecting his dairy farm. “We see the loss in the economy since we’ve lost the service to the railroad,” he said.
The video aired on cable television, which was only available in Manhattan at the time. He watched the premiere from his aunt’s city apartment, surrounded by friends and bottles of wine.
“This must be what the Beatles felt like the first time they heard one of their songs on the radio,” he remembers thinking.
The film was also screened at The Moviehouse in Millerton for a one-night showing.
Though Milano didn’t pursue filmmaking after NYU, he stayed rooted in the area, opening Milano’s Restaurant in Pine Plains, which operated for 14 years. The location is now home to Back Bar Beer Garden.
Nearly 50 years later, Milano says he is content with how history unfolded. “If the trains had stayed, this whole area would look completely different,” he said. “In a way, I’m glad it didn’t happen because I still like bouncing along these scenic back roads. It’s one of the prettiest parts of New York.”
According to “A Beckon Call to a Village,” a 2001 history compiled by former North East Historical Society president Diane Thompson, leaders in the already-established Town of North East understood the opportunity a rail line could bring.
A meeting was held at the Wakeman House, home of local farmer Walter Wakeman, where a small group of men began laying out plans for a village that did not yet exist.
Wakeman himself played a crucial role, selling a 66-foot strip of his farm – nearly half a mile long – to the railroad. Additional acreage followed to accommodate a depot, engine house, sheds and extra track.
Civil engineer Sidney Miller is credited with bringing the railroad to what would later be known as Millerton in 1851. According to historical documents, he was so well regarded that the village was named in his honor.
On Sept. 1, 1851, the first train rolled into Millerton.
Two men pose with a mile marker noting the distance from Millerton to New York City.Courtesy U.S. Library of Congress
Iron production also played a key role in Millerton’s early growth. In 1854, the Millerton Iron Company established a major foundry in the area known as Irondale.
By 1882, the plant employed about 150 workers and by 1890 it was producing up to 12,000 tons of pig iron annually. The raw iron was used to manufacture cast-iron products, including railroad car wheels.
Irondale grew into a small industrial hamlet with a general store, grist mill and post office.
With the railroad established, Millerton quickly expanded. In 1852, just one year after the first train arrived, the Millerton Hotel was erected on North Center Street behind what is now the Oakhurst Diner. Built by Alexander Hawley, Alexander Trowbridge and James Winchell, the two-story building catered to rail passengers and visitors.
The hotel was later acquired by A.J. Pulver, who modernized it. For roughly 50 years, it stood as a symbol of Millerton’s growth before being dismantled in 1936. Its materials were salvaged during the Great Depression.
That early period saw the construction of a Greek Revival-style commercial building that housed E.W. Simmons & Co., Millerton’s first general store. Opened in partnership with Harvey Roe of Spencer’s Corners, the store sold groceries, lumber and building supplies.
A historical photograph depicts Millerton’s Methodist church on Main Street ca. 1910.Courtesy U.S. Library of Congress
By the mid-1860s, Millerton’s commercial district continued to expand. In 1865, prominent builder Ambrose Beers constructed an Italianate-style carpenter shop that would later become home to Dewitt “Dewey” Husted and his wife. For 18 years, it operated as a confectionery and bakery. It later served as a sporting goods and furniture store, and after a 2008 renovation is now home to Elyse Harney Real Estate.
By 1875, Millerton was formally incorporated and recognized as a municipality. Kneeland J. Munson became the village’s first mayor.
In just 24 years, Millerton had transformed from farmland to railroad outpost to incorporated village, with even greater expansion waiting in the decades to come.
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Hotchkiss Library’s Book Signing Weekend draws readers of all ages
One notable local author was former Secretary of State and Secretary of Defense under Presidents Richard Nixon and Gerald Ford, Henry Kissinger. Authors from farther away have included Pulitzer Prize winner and former executive editor of The Washington Post and The Boston Globe, Marty Baron, Bard College writer-in-residence Francine Prose and National Book Award winner Susan Choi.
2025’s Hotchkiss Library of Sharon’s Summer Book Signing WeekendStephanie Stanton
This year’s featured headliner was scheduled to be E. Jean Carroll, whose book “Not My Type: One Woman vs. a President” chronicles her legal battles with President Donald Trump. Unfortunately, another legal decision was issued in her favor in June, sparking outrage and violent rhetoric from some Trump supporters. Consequently, Carroll’s appearances have been canceled.
But there is still plenty to be excited about at this year’s Book Signing Weekend, and a lot of it has to do with food. For years, the weekend has featured Author Dinners, intimate gatherings hosted by library patrons in their homes in Sharon and neighboring towns. Among the authors attending these dinners are travel writer and influencer Jennifer Broome, geneticist and internationally recognized anti-racism educator Shaumita Dasgupta, and Russian-born New York Times bestselling novelist Gary Shteyngart.
The dinners, however, are just the beginning. On Saturday, the library will host its second annual Page to Plate, a literary celebration of food.
Throughout the day, attendees can enjoy talks, demonstrations and perhaps even a cocktail or two from chefs, bakers and, of course, writers.Featured guests include novelist Adam Roberts, author of “Food Person: a Novel”; Bread Alone founder Daniel Leader; and Chris Morocco, food director of Bon Appetit and Epicurious. Programming is divided into morning and afternoon sessions, with tickets available for either session or the full day.
Of course, the main event is the book signing itself, when dozens of authors will sign books available for purchase at the library.
For tickets, visit hotchkisslibraryofsharon.org
Owners Asio and Angela Highsmith
Asio’s wife Angela, a California native drawn to nature, had spent years bringing their children to the Berkshires. The family already owned property there, and the pandemic simply accelerated the move they were already considering. Their son summed up the family’s feelings best when he was 5 years old. “He said, ‘I want to be in a place where there’s more trees than people,’” Angela recalled.
The move wasn’t motivated by business ambitions. In fact, neither Asio nor Angela intended to become entrepreneurs again. “We came up here for the outdoors and for the beauty,” Angela said. The espresso truck emerged almost by accident. When old café equipment began taking over their basement, Angela suggested putting it on a truck.
“That’s exactly what happened,” Asio laughed. What began as a practical idea soon evolved into something much larger.
To find out where the Best Damn Espresso truck will be on any given morning, text ‘BDE’ to 844-659-1203Provided
Asio brings decades of hospitality experience to the business. A lifelong bartender and mixologist, he approaches espresso the same way a master cocktail maker approaches a drink — with precision, intention and respect for the craft.
“Coffee means community,” he said. “It’s a big part of the hospitality vision that my wife and I want to bring to the world.” For Asio, every drink matters. “My motto is one drink at a time,” he said. “I focus on what’s in front of me.”
That philosophy extends beyond the espresso machine. Customers aren’t simply buying a beverage; they’re entering an experience shaped by two people who view hospitality as an act of service. “Food is magic. Coffee is magic,” Asio said. “It’s an exchange of great energy.”
Angela, who often works the front of the truck, describes the customer relationship in similar terms. “When someone comes to the truck, you’re hosting them,” she said. “You’re entertaining them. You’re giving them exactly what they want.”
Despite doing almost no traditional marketing, Best Damn Espresso has developed a devoted following throughout the region. Asio attributes that growth to consistency rather than promotion. “Advertising is overrated if your product is mid,” he said.
The name itself — Best Damn Espresso — is intentionally bold. Many businesses would hesitate to make such a claim. Asio sees it differently. “It’s actually me challenging myself,” he explained. “Every time I look at that truck, I see ‘Best Damn Espresso.’ The aspiration for being great at what we do happens every day.” That relentless pursuit of quality appears to resonate with customers.
Four years after launching, the company has expanded from a single truck to multiple units. Yet despite the growth, Asio and Angela remain focused on maintaining the same personal connection that defined the business from the beginning. They have also become unexpected pioneers in the local food-truck scene. “There wasn’t really a food truck presence in Great Barrington before we started,” Asio said. Today, several food trucks operate in the area, some inspired by their success. “The benefit is inspiring someone,” he said.
To receive daily updates on the truck’s location, customers can text “BDE” to 844-659-1203.
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