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Spooky Tales From Cheshire, Past And Present

Spooky Tales From Cheshire, Past And Present


Halloween has this way of bringing out the kid in all of us.

According to the National Retail Association, Americans, on average, spend $9 billion per year on the holiday, surpassed only by Christmas spending, which eclipsed the $1 trillion mark just last year.

Costumes, decorations, and candy make up the bulk of the spending, with adults just as likely to go all-in on the holiday as are little trick-or-treaters.

As we all know by now, the pandemic of 2020 has changed everything and it’s impossible to know exactly what impact our current public health crisis will have on normal Halloween habits. There will likely be few, if any, traditional parties held and fewer little “monsters” are expected to roam the streets this Oct. 31 for trick-or-treating.

But that doesn’t mean we can’t all enjoy another tradition this time of year: A good scare.

Whether it’s settling in for a horror movie marathon or sharing a few ghostly tales of our own, October is the time of year when we become keenly aware, even intrigued, by what it is that may be going bump in the night.

Cheshire, settled in 1694, has had plenty of time to accumulate tales of unusual happenings and strange sightings. Old houses tend to have a few more creeks and unusual sounds emanating from the basement, and particularly dark, lonely nights seem to draw out the spirits.

The website, Ghosts of America, is a repository for spooky stories recounted by the people who have experienced them firsthand. A search for Cheshire reveals that several residents have recorded any number of unusual encounters over the years — some simply intriguing, others downright frightening.

For instance, a resident named Anthony describes how, one Christmas many years ago, he was setting up decorations in his Cheshire home when he turned suddenly to see two misty figures standing before him. They appeared to be a father and a daughter — the father dressed in a polo shirt and black pants while the young girl wore a white dress. The two eventually disappeared, and Anthony does not share whether his father/daughter interlopers ever appeared again.

A Mountain Road resident, who wished to remain anonymous, spoke of how, for 9 years they and their family lived in a home teeming with paranormal activity. “I don’t know how I lived in that house for that long,” wrote this anonymous Cheshirite. Throughout their stay, scratching could be heard on the windows and banging on the door that led from the kitchen to the basement. Perhaps something was trying to get in … or get out?

Blake wrote about an experience at the historic Hitchcock-Philips House, home to the Cheshire Historical Society: 

“I snapped a picture and saw an orb next to a chair. This being my second visit, I wasn’t surprised. The last time (I was in the house), I had felt eerie cold spots and spider webs that, when I looked, weren’t there. 

These are both signs of an intelligent ghost … or are they? If you want to see for yourself, be wary: in the year 1799, Hannah Hitchcock and her baby both died during childbirth inside the home. You never know — you may see Hannah wandering around in her wedding gown or (hear) her child giggle and run down the stairwell.”

The Historical Society boasts of its mission to keep local history alive. Having a few ghosts knocking about may be one way of doing that.

Have you been to the woods off of Fernwood Lane? According to a resident named Eva, they are “absolutely terrifying.” 

“(Poltergeists) frequently tormented my family in the house” near the woods, explained Eva. It left her and her family feeling a “overpowering sense of fear” while in the house. If anyone happens to be from the Fernwood Lane area, it might be best to avoid the woods if you’re worried about an unwanted visitor following you home.

Of course, not all of Cheshire’s stories involve the paranormal. Take the strange story of the man who, in the 1870s or 1880s, was out on a hot summer afternoon shingling his Cheshire Street home. According to legend, the man suffered a serious case of sunstroke and “lost his mind and his speech.” However, what he didn’t lose was his ability to whistle. 

Edwin Brown, who wrote “A Record of Cheshire Street and Its Earliest Settlers” in 1888, described the man as a “mindless wanderer” who said nothing from that day forward, but could be heard whistling his way up and down the neighborhood streets.

Can whistling still be heard, from time to time, in the Cheshire Street area? Keep your ears open.

And no retelling of Cheshire spooky stories is complete without that of the Kye Witch. 

Approximately 30 years after the Salem Witch Trials, accusations of witchcraft were few and far between, but that didn’t mean settlers, like the good folk of Cheshire, didn’t still believe in their existence. Around 1724, the widow Kye sat in her small, dilapidated home on Cook Hill Road, alone and with no friends of which to speak. As the years went by, rumors circulated that she was more than just a solitary old woman but, in fact, a witch — one who perhaps had a closer-than-desired relationship with all those bumps in the night.

As the famous Cheshire tale goes, one evening, Nathaniel Ives and his wife were suddenly filled with the desire to display some good ol’ New England hospitality. Despite the rumors, it would seem that Mrs. Ives was undeterred. She and her husband would reach out and offer their kindness.

As the two approached the old woman’s home late one evening — why the Ives chose a dark night to pay a visit to a rumored witch is lost to history, but certainly helps set a more dramatic scene — Nathaniel expressed misgivings about “calling on folks that are suspect of having the ‘old nick’ in them.” Mrs. Ives reportedly chastised her significant other, reminding him that “’Tain’t for us to say who dealt with Satan. There’s more than this Kye-Witch that do it, heaven knows.”

Within sight of the home, they were surprised to hear it bursting with life. It sounded as if a party were in full swing, complete with talking, dancing, singing, and a fiddle being played. The two approached the door with their gifts of hospitality in hand, and Nathaniel reluctantly knocked.

Immediately, the lights went dark, the noise stopped, and everything went silent. It appeared as if no one was home. 

The suddenness of the change petrified the Ives, who reportedly pushed the front door open a crack, left their gifts, and hurriedly fled back to their own home.

The story became famous, so much so that it was recounted in the Reverend E. C. Baldwin’s early account of local history entitled “Home World,” published in 1886. Passersby made sure to give the Kye Witch’s home a wide berth and children on their way to and from school knew better than to linger in front of that particular home. No one ever called on the widow Kye, for anything.

Rumors circulated that a child had been killed in that home and buried beneath bushes. Some residents even insisted that, on a clear, quiet night, you could hear the ghost of the child crying.

Could they have been right? Can the strange sounds of quiet crying still be heard to this day?

What other spooky tales are hiding in Cheshire’s past? 

As we approach Halloween, it might be a good time to check the attic or basement one more time before heading to bed. And of course, check under your covers and inside the closet before sliding off to sleep.

Happy Halloween!


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