Halloween on the Chester Green lures goblins big and small

Halloween event organizers from left, David, Angel and Julian Sottovia in front of their shop, Matilda and Three Bears. Click the photo to launch the gallery. All photos by Paul Wein.

By Paul Wein
©2026 Telegraph Publishing LLC

Something special and spooky was happening on the Chester Green on Saturday night. The air was brisk as the sun began to sink lower in the October sky; cold enough that this reporter almost decided to go back to his car for his winter coat.

Seeing more rugged Vermonters in T-shirts or dressed as cheerleaders gave me pause. Who among us older ones can forget the shame of having to wear a coat over our super-cool costumes? I left my winter coat where it lay, my pride, for the moment intact.

Chester Firefighter Tom Cutler, right, hands out candy and memories to three future chiefs.

Children were mostly still in costume, candy from the earlier Trunk or Treat event likely stashed in their parents’ car. This was almost an after-party for them. Candy, of course, is the main event for the kids  — and the kids at heart. As the chill settled in, it was time to eke out a little bit more fun and costumed adventure.

While the adults chatted and chomped barbecued turkey legs, kids climbed into the fire engine and other emergency vehicles, thanks to the Chester Public Safety Department. As darkness fell and older trick-or-treaters filled the sidewalks, police cruised slowly along Main Street, lights flashing, reminding motorists to stay aware of the foot traffic and letting the costumed children know that they were watching, doing their best to keep things safe.

One couple and their hot dog are ready for the Pet Parade.

Meanwhile, at the far end of the parking lot, farther from the food booths and the upcoming pet parade, I spied what appeared to be a riot or melee of some kind occurring.

Goblins, witches, and fairies of all sizes were swarming a table full of small, furry creatures. I approached them warily, unsure if they were landsharks in some sort of Halloween feeding frenzy, the likes of which I had never seen. Relief spread as I got closer; these were not real goblins and fairies; they were children in costume, happy, laughing children. The small, furry creatures on the table, and now in every child’s hands, were teddy bears: the best breed of teddy bears — free ones!

I soon learned of a very special tradition kept here in Chester. Something unique, started years ago by Georgette Thomas, the late owner of The Hugging Bear Inn and Shoppe on Main Street, now a private residence. Every Halloween, Thomas, who played host to Steiff Bear events and whose shop was stuffed with toy bears and other animals, would give away coveted Beanie Babies to every child who came to her door.

This night, Kristen Merrow was manning the table loaded with free bears, carrying on Thomas’s beloved tradition. Many of the parents who brought their children to Merrow’s table had, as children, visited the Hugging Bear on Halloween for a free bear themselves. Merrow said that at one time Thomas housed over 10,000 teddy bears at the Hugging Bear.

Kristen Merrow, far left, keeps the Teddy Bear table full and the memory of Georgette Thomas alive.

Georgette “Georgie” Thomas passed away in 2014 at the age of 83. By all accounts, she was a happy, highly accomplished and well-loved woman. I wondered, as I made my way back to my car and its heated seats, how many of these children would return in 15 years or more with their own children, to pick out a free bear.

Like the police officer patrolling the streets of Chester, the smiling firefighters handing out candy and helping a little girl into the seat of their fire truck, and like the shivering parent waiting on the sidewalk while their child hollers “Trick or Treat!” at a neighbor’s door, the legacy of a kind woman who lived across the street and whose hometown knew her as “The Teddy Bear Lady” all are a part of the fabric of Chester. A very fine fabric; a very warm fabric on this chilly last night of October.