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Thumbing through the photo archives: The ‘Southern Berkshires Through Time’

In “Southern Berkshires Through Time,” Leveille has examined almost 200 sites, ranging from historical homes, businesses and intersections, to one of Leveille's other passions: unusual rock formations.

Great Barrington — One of the great pleasures of living and working in the Berkshires is getting to read the works of people who write about the region’s past with such affection. There are numerous local historians who continue to do a great job of chronicling southern Berkshire County and beyond.

Many, including Bernie Drew, Carole Owens and Rick Wilcox, write regularly for The Edge. Yet another, Gary Leveille, writes satirical pieces for us occasionally but also stays busy working as the archivist for the Great Barrington Historical Society and writing books about the southern Berkshires such as Around Great Barrington, Legendary Locals and Old Route 7 – Along the Berkshire Highway.

Gary Leveille in his library. Photo: David Scribner

His latest, the Southern Berkshires Through Time, is another gem. It’s sort of an extended variation of Then and Now, a regular column Leveille has produced for the Berkshire Record for several years. In Then and Now, Leveille takes a modern-day photo of a familiar place in the southern Berkshires and juxtaposes it with a historical image of the same site, adding a couple of elegant paragraphs explaining the difference between the two eras. Some of the pairings in his new book are from past Then and Now columns but most of the them are brand new. 

“It’s bite-sized bits of history that tell a story in a concise way,” Leveille said in an interview.

In “Southern Berkshires Through Time,” Leveille has examined almost 200 sites, ranging from historical homes, businesses and intersections, to one of Leveille’s other passions: unusual rock formations. 

“I’ve always been a bit of an explorer — everything from caves to rail trails,” Leveille said.

The full cover of Gary Leveille’s ‘Southern Berkshires Through Time.’

The iconic cover will really catch your eye; it’s the facade of what is now known as the Barrington House on the west side of Main Street. The 1912 historical photo at the top of the cover captures the same building but it is scarcely recognizable in its previous incarnation as the Miller Hotel. Porches overhang the sidewalk and the front of the mostly white hotel is lined with an assortment of what are now vintage vehicles. 

Leveille’s love for the Berkshires has a somewhat unorthodox beginning. He grew up in Cheshire, Connecticut, near Waterbury, but his parents were from western Massachusetts.  

He first set foot in Berkshire County in the summer of 1964 — in fact, the day after President Lyndon Johnson signed the Civil Rights Act — when his parents took the 11-year-old Gary camping at Prospect Lake Park in North Egremont. Ironically, the legendary civil rights leader and Great Barrington native W.E.B. Du Bois had died the previous year, lending additional local gravity to the landmark legislation. 

Leveille immediately fell in love with the campground, Egremont and the southern Berkshires. “My sister and I made it known that we loved this place and wanted to return – soon!” Leveille wrote in the preface of one of his other local history books, The Eye of Shawenon, which is a history of the area around Prospect Lake.

But moreover, later in his life when he became a writer, Leveille wrote about the region every chance he got. That wasn’t as often as he would have liked because his career as a corporate copywriter was growing.  

Indeed, while at Milton Bradley, Leveille ghost wrote a 1989 letter signed by then-real estate developer Donald J. Trump that appeared in every box of the now-defunct Trump: The Game, a board game similar to Monopoly but with the name and image of the future president of the United States on the box. But the allure of local history would not loosen its grip.

“For me, researching history — especially through old photographs and documents — opens up a window into the past that I find irresistible and compelling,” Leveille said. “It is an exciting and unique way to explore our Berkshires.” 

A trolley makes its way down Main Street in Great Barrington. Courtesy

When Leveille settled on the concept for “The Southern Berkshires Through Time,” he set about trying to organize it. Which towns constitute the southern part of the county, for example, and how would be photo pairings be laid out? 

After considerable debate, Leveille and his publisher, Fonthill Media, Inc., settled on Great Barrington, Egremont, Lee, Sheffield, Stockbridge — and perhaps to a lesser extent, Alford, Monterey, Mount Washington, New Marlborough, Otis, Sandisfield, Tyringham and West Stockbridge. 

One of the most interesting photos is not actually paired but rather on a single page before the main event begins. Taken during the winter of 1865, it’s one of the oldest known photos of downtown Great Barrington. 

A group of sleighriders who were being pulled by a team of mules took a moment to pose in the middle of a snow-covered Main Street. Abraham Lincoln was still president and only a few weeks away from his death at the hands of John Wilkes Booth at the Ford Theatre. 

The only recognizable structure — indeed the only building still standing from those days — is the building that now houses T.P. Saddleblanket at the intersection of Main and Railroad streets. It’s known as the City Store building and, built in 1853, it’s believed to be the oldest surviving commercial structure in town, having survived the famous 1896 fire that destroyed both sides of Railroad Street. 

“No traffic. No crosswalks. No Problem,” reads the caption. 

And for some of the “now” photographs a great deal of patience was called for. A 100-year-old photo of a locomotive crossing Cherry Street in Stockbridge called for a modern version with a Housatonic Railroad engine crossing the road at the same point. So Leveille had to be there at just the right time. 

“That was one of my favorite shots but it took several weeks, if not months of work, to make that happen,” Leville explained. “I had to contact Housatonic Railroad. Their schedule changes weekly.”

The underpass in Housatonic, allowing the trolley line to pass under the New York, New Haven, and Hartford tracks.

There are numerous photos of downtown Housatonic before it was burned — not once but twice — and images of structures long since gone: trolley trains in Housatonic, Great Barrington, Stockbridge and Egremont; the Jug End Resort in Egremont; the old mill pond at Monument Mills in Housatonic; the enormous Berkshire Woolen Mill, a stone behemoth at the north end of Main Street in Great Barrington, where Caligari’s is now and diagonally across the street from Domaney’s. And of course, the Great Barrington Fairgrounds are seen in happier times. 

The photographs in the book cover the last 150 years. But Leveille says the “classic beauty” of the southern Berkshires has drawn photographers since the camera was first invented.

“Vibrant villages have evolved over the decades, even as the surrounding scenery remains breathtaking,” he writes. “Once thriving textile mills have been replaced by innovative tech enterprises.” 

The once vital paper industry, with its enormous mills in Lee and Housatonic, has survived but in a diminished capacity. But even with industrial decline, “year-round recreational and educational opportunities have blossomed.” Even so, what Leveille calls a “magnificent menagerie of historic homes, prosperous farms, and top-notch cultural venues” survive.

The images are courtesy of, a digital collection of vintage photos and illustrations Leveille has purchased or borrowed from public or private collections.

My only criticism of the book is it’s not easy to look by subject. It is not organized by town, in part, Leveille says, because that would take additional pages — and also because it would detract from viewing the southern Berkshires as one region. 

Nor is there an index. So if you want to find something, you’ll just have to flip through the pages. But I don’t think you’ll mind that because, in the course of flipping, you’re bound to find something you didn’t expect.

“The images and interesting narrative inside this book offer a rare glimpse of the Southern Berkshires through time,” Leveille says in the jacket. “By looking at the whole picture, the connections between our past and present will become apparent.”

Truer words were never written.


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