October 30, 2011

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

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.