Long before the bustling Harlem Valley Rail Trail hosted runners, walkers and cyclists, a historic railroad ran through Millerton, connecting rural towns to New York City. The eventual dismantling of the railroad was met with criticism and pushback from residents.
That chapter of local history comes alive in a resurfaced documentary film that had been tucked away in an attic in Dover Plains for more than 40 years.
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.

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.”









Madeline Hartwell, left, visits Tom Hall’s vendor tent along the Harlem Valley Rail Trail during The Voice of Art’s Fine Art Festival in Millerton.Photo by Nathan Miller

















