October 30, 2011

The Quaintest/Creepiest New England Town You Could Ever Hope to Visit in October

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Quaint because of the Victorian architecture, the locals who all seem to know each other by name and the one main drag that is home to the majority of the town's shops, cafes and restaurants. 

Creepy for the same reasons.

Welcome to Chester, Vermont

Technically speaking, Chester is a village; a village that packs a population of just 3,000 into a whopping 56-square-mile landmass. If you're looking for solitude, simple living and a setting for a Stephen King-esque horror novel, Chester could be the place for you.

The village, which is located in southern Vermont's Williams River Valley, boasts two historic districts (Stone Village and South Village), two gas stations and zero stoplights.

Driving from Boston to Green Mountain National Forest for a weekend of hiking, Chester was an unexpected stop along the way. There was a certain eeriness -- and charm -- to the village that made me want to explore. Maybe it was the old cemetery, the gingerbread-style houses or that long row of storefronts, complete with a grandiose Masonic lodge. 

Courtesy of explorah

Courtesy of

Strolling through the Vermont village, it was hard not to notice the old man with the long, white scraggly beard reading on a bench next to the cemetery. He seemed more like an apparition than a living, breathing person; just another part of the historic scenery, like the statue that was standing guard a few yards away.

Inside a Chester cafe, the man behind the counter was addressing customers by name and pointing out changes in hairdos and wardrobe selections. It became obvious that the same patrons came to this cafe day after day, week after week, month after month.

While heading back to the car, Chester offered one last eerie surprise, which immediately got me thinking of The Shining: twin girls in matching outfits, both riding scooters down the sidewalk.

I swear one of them looked at me and mouthed the words, "red rum," as I disappeared down the road and made my escape from the quaintest/creepiest place I had ever visited.


  1. I grew up there and raised 3 children never thought of it as creepy.Though it does have its stories...

  2. I grew up there too, started a horror novel set there but never finished it. Just went back there and it was like being in a time warp. Got a history book to use as fodder to revive the horror novel... hehe

  3. ha, we probably know each other

  4. Hahahahahahaha. I grew up in Chester. My folks still live there & this is one of the funniest articles I have ever read about my hometown. Thank you Bard of Boston! You are a true Masshole & should be proud of it!

  5. Creepy!!! Haha. Only time it's creepy is when the creeps from Mass congrats the roads on their way to Okemo. I grew up here as well, used to now and bury the dead in those cemeteries while in high school. The author should explore Mass a little more, like Salem. Now that place really IS creepy.

  6. I grew up in Chester, but out side the village on a dairy farm. The village wasn't what it is today. Only stores we had back then were a drug store, an IGA (where the book store is now), Gould's market, and the Inn on the Green. O, I forgot we did have a movie theater upstairs in the building next to the Episcopal Church, which cost us 25 cents for a bag of popcorn and a matinee to see The Lone Ranger, or Roy Rogers. Now, Them's the days.