Thank you!
Your support is sustaining the future of local news in our communities.

Remembering the origins of annual Railroad Days fest

NORTH CANAAN — With the advent of North Canaan’s 59th annual Railroad Days, Kathryn Boughton, Canaan’s Town Historian, recollected the festival’s origin and early years. Though she was away at college when the town held the very first festival, in 1964, by the time she had returned, Railroad Days was already and integral part of town tradition and community.

The Chamber of Commerce concocted Railroad Days as a commercial venture, a way for shops to empty out their summer inventory with bargains, and to give the local merchants a needed boost. Food and events, as well as sidewalks lined with tables of goods for sale, brought the tourists and residents to the town center.

From the beginning, “it had a very festive feel to it,” said Boughton. “The street looked gay! And you know, there’s nothing like a the chance to get a bargain.”

For decades, the town’s railroading history provided the central theme for the 10-day festival. Scenic excursions on the train were a centerpiece, and remained one of the most popular attractions until, due to liability issues, they were discontinued in the 1980s.

Canaanites often insist that without the railroad, there would be no Canaan. Before 1840, the “town” consisted of the Gillette property, up on the northwestern town line, and Lawrence Tavern, down by Lower Road, on the banks of the Blackberry River. Just 12 years after the trains arrived in Canaan, a nucleus of businesses had formed just west of the tracks, forming a nascent town center.

Through the WWII era, the village served as a cultural hub, where townspeople gathered to exchange news and talk, and visit the shops on Friday evenings. The plaza in front of the train station, hung with strings of painted lights, hosted dinners and dances on warm nights. At the town center, shops and businesses served as a cultural hub, where the town gathered to exchange news and talk on Friday evenings.

“All the farmers would come in, and it might be the only time all week long that they saw anybody off the farm. So their wives would get all dressed up—you didn’t go into town looking like a farmer!” People went shopping and socialized, walking up and down the streets, stopping in stores like Fuller Hardware and, “just chatting,” not always buying, said Boughton, quoting

Fred Hall, who ran the hardware store and before becoming a town historian. “But he said, ‘I didn’t care! It was fun to have them in the store.’”

Following the war, however, Canaan’s demographics—and subsequently its commercial landscape—underwent dramatic change. “After two decades of depression and war, people were just bursting to get in the new car with their new tires and go somewhere else,” said Boughton.

The onset of American car culture reshaped not just the demographics, but the landscape of the town itself. As the money drained from Canaan with the departure of the well-

to-do, the onset of American car culture was reshaping not just the demographics, but the literal town as well.

“What happened here was the same as what happened at town centers and in cities across the country,” said Christian Allyn, who, a lifelong Canaan resident who recently became a Canaan Selectman. In the 60s and 70s, “there were movements to level a lot of the buildings and put up shopping centers.” The exploding prevalence of cars also meant that the passenger trains were being used less and less.

“There used to be stores all along Main Street,” said Boughton. “I can’t tell you how many times I tell my students, ‘Well, this building was here, but now there’s a parking lot.’ You know, it’s like that old Joni Mitchell song.”

It was in this less-bucolic context, a challenging period in the town’s history not so different from those that Canaan has faced in more recent years, that the Chamber of Commerce came up with Railroad Days, hoping to boost commerce and bring people back into town.

During the depression of the 2010s, when Canaan was suffering severe economic stress, the annual Firemen’s Carnival was rolled into Railroad Days, preserving Canaan’s summer carnival while those in nearby towns continued to falter and shut down.

“Roughly 30 years ago, every town in the area had a carnival in some form,” said Allyn.

“Ours is one of the last ones. You get people coming from quite a distance.”

Since its inauguration, said Allyn, the festival has provided more than just fun and celebration for Canaanites; it also occasions a moment of unity and town pride, even—and perhaps especially—during stressful times. The focus of Railroad Days has evolved from its commercial origins to center much more on community celebration.

“They started out just trying to bring people into the town center for a hoopla party,” said Boughton. “And it’s still really a pretty good party!”

Latest News

Sharon voters reject controversial school budget, 114-99

The May 8 town meeting and budget vote were moved from Sharon Town Hall to Sharon Center School to accommodate what officials said was the largest turnout for a Sharon budget meeting in recent years.

Alec Linden

SHARON – More than 200 residents packed the Sharon Center School gymnasium Friday, May 8, where voters narrowly rejected the Sharon Board of Education's proposed 2026-2027 spending plan by a vote of 114-99, sending the budget back to the Board of Finance after weeks of heated debate over school funding.

The rejected proposal – the ninth version of the budget since deliberations began months ago – carried a bottom line of $4,165,513 for the elementary school, unchanged from last year. The flat budget came after the BOF ordered the BOE in early April to remove nearly $70,000 from its spending plan.

Keep ReadingShow less

Liane McGhee

Liane McGhee
Liane McGhee
Liane McGhee

Liane McGhee, a woman defined by her strength of will, generosity, and unwavering devotion to her family, passed away leaving a legacy of love and cherished memories.

Born Liane Victoria Conklin on May 27, 1957, in Sharon, CT, she grew up on Fish Street in Millerton, a place that remained close to her heart throughout her life. A proud graduate of the Webutuck High School Class of 1975, Liane soon began the most significant chapter of her life when she married Bill McGhee on August 7, 1976. Together, they built a life centered on family and shared values.

Keep ReadingShow less
‘Women Laughing’ celebrates New Yorker cartoonists

Ten New Yorker cartoonists gather around a table in a scene from “Women Laughing.”

Eric Korenman

There is something deceptively simple about a New Yorker cartoon. A few lines, a handful of words — usually fewer than a dozen — and suddenly an entire worldview has been distilled into a single panel.

There is also something delightfully subversive about watching a room full of women sit around a table drawing them. Not necessarily because it seems unusual now — thankfully — but because “Women Laughing,” screening May 9 at The Moviehouse in Millerton, reminds us that for much of The New Yorker’s history, such a gathering would have been nearly impossible to imagine.

Keep ReadingShow less
google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.

By any other name: becoming Lena Hall

By any other name: becoming Lena Hall

In “Your Friends and Neighbors,” Lena Hall’s character is also a musician.

Courtesy Apple TV
At a certain point you stop asking who people want you to be and start figuring out who you already are.
Lena Hall

There is a moment in conversation with actress and musician Lena Hall when the question of identity lands with unusual force.

“Well,” she said, pausing to consider it, “who am I really?”

Keep ReadingShow less
Remembering Todd Snider at The Colonial Theatre

“A Love Letter to Handsome John” screens at The Colonial Theatre on May 8.

Provided

Fans of the late singer-songwriter Todd Snider will have a rare opportunity to gather in celebration of his life and music when “A Love Letter to Handsome John,” a documentary by Otis Gibbs, screens for one night only at The Colonial Theatre in North Canaan on Friday, May 8.

Presented by Wilder House Berkshires and The Colonial Theatre, the 54-minute film began as a tribute to Snider’s friend and mentor, folk legend John Prine. Instead, following Snider’s death last November at age 59, it became something more intimate: a portrait of the alt-country pioneer during the final year of his life.

Keep ReadingShow less
Sharon Playhouse debuts new logoahead of 2026 season

New Sharon Playhouse logo designed by Christina D’Angelo.

Provided

The Sharon Playhouse has unveiled a new brand identity for its 2026 season, reimagining its logo around the silhouette of the historic barn that has long defined the theater.

Sharon Playhouse leadership — Carl Andress, Megan Flanagan and Michael Baldwin — revealed the new logo and website ahead of the 2026 season. The change reflects leadership’s desire to embrace both the Playhouse’s history and future, capturing its nostalgia while reinventing its image.

Keep ReadingShow less
google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.

google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.