By Samantha Russell

WESTPORT — A week before Halloween, nine people spent their Friday night learning about shadowy incidents from the town’s past during a “Dark History Walking Tour” organized by the Westport Museum of History and Culture.

The hour-long tour, led by Nicole Carpenter, the museum’s assistant director, began and ended on the museum’s Avery Place brick walk. Participants visited five places downtown with historical meaning and significance — and an eerie element in keeping with the spirit of Halloween approaches.

“We explore the darker sides of Westport when it’s in people’s minds,” said Carpenter. Friday’s event is one of seven tours sponsored by the museum — the only one in the evening and part of its “Spooktober” series. 

Across the street from the museum, Town Hall was the first focus of the evening. Carpenter discussed Charles Diedrich and the Synanon rehabilitation program that evolved into a cult, which began in California but quickly spread as followers increased in the 1950s. Synanon bought a house in Greens Farm where it operated a business and drug rehabilitation center. When it was determined the group violated zoning laws in a residential area, however, town officials halted the operation and Synanon vacated the property.

Carpenter added that the unsettling problem with Synanon was members inability to leave, often losing their assets or becoming the victims of violence from fellow cultists. One former member had his skull “cracked open” during a beating, she said, and credited the town administration at the time for preventing the group from becoming established in the community.

The next stop on the tour took a turn down Main Street where the Brandy Melville and Catherine H. stores now stand. Carpenter noted the building used to be a school where a “very strange occurrence” took place when 18-year-old Mary King suspiciously died with no revealed cause of death.

King was social, lively and healthy, according to Carpenter, and attended a dance at a nearby, downtown hotel. After the dance, she returned to the school and was found dead at 2 a.m. The woman who checked on her, Mrs. Killen, also suddenly disappeared. 

Following this stop, Carpenter led the tour to the outside of the Anthropologie store at Bedford Square to discuss Westport’s Prohibition era, which lasted from about 1920 to 1933. “Westport exceeded the riotous [activity] of New York,” Carpenter said about the town’s prohibition infractions. In a six-month period during the start of Prohibition, the town of Fairfield had about a dozen infractions; Westport, on the other hand, recorded more than 600 in that same time period, she said.

During Prohibition, the site of the Anthropologie building at the time was the Westport Hotel, which in 1922 was raided for violating the anti-alcohol laws.

Walking across Main Street and down to the Saugatuck River banks, the tour transitioned from a discussion about alcohol to one about death. With the mass casualties created by the Civil War, bodies needed to be shipped home along the river for burial. Production of combat weapons and chemicals skyrocketed and with it the addition of Westport manufacturing businesses along the river. 

Waste from manufacturing facilities ended up in the Long Island Sound which, according to Carpenter, many native Westporters can recall.

The final tour stop before returning to the museum was Gorham’s Bridge and Gorham Island, detailing the fatal shooting by Brendan McLaughlin of his father at their island home in 1961. Afterward, the McLaughlin house stood abandoned for two decades, and later was purchased by the town. Despite ongoing discussion about what to do with the building, it was suddenly demolished, unwitnessed, in the middle of the night. 

Some Westport locals claim the island, now the site of an office building, is haunted. 

Back at the museum, Carpenter concluded the tour with stories about paranormal activity within its perimeter. One staff member claimed to have seen the apparition of a man, apparently from the Colonial era, at the top of a stairway, and another said she felt a hand on her shoulder while no one was around. Carpenter warned her listeners to stay away from the stairs, where most of the paranormal activity has been felt.

Robert Mitchell, former chairman of the museum, was on the tour and said that he “always loves Nicole’s tours” and her storytelling abilities. 

“I knew some of the stories, but some I didn’t,” he said, crediting Carpenter for her research. “I didn’t know anything about Gorham Island, for example.”

Westport resident Alexandra Pearson also enjoyed the experience. “I thought it was great,” she said. While the Dark History Walking Tour was the first of the museum’s tours she has taken, she hopes to join more of the tours in the future.

“I felt like there were a lot of interesting tidbits of information … I learned a lot,” she said. “We moved to Westport a year ago, so it’s nice to learn the history of our town.”

Samantha Russell is a Westport Journal intern.