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HomeLife In the BerkshiresDowntown goblins and...

Downtown goblins and ghosts : A Great Barrington Halloween tradition — ‘It’s glorious’

"This event provides our students with the much needed opportunity to contribute their skills and energy to the supportive community where they live." -- Neel Webber, Monument Mountain Regional High School art teacher

Great Barrington — It’s an annual sight and has been for as long as anyone can remember. But pedestrians and motorists still react with surprise at the student artists who set up shop downtown on one day the week before Halloween.

Student Halloween artwork decorates the windows of Robin’s Candy Shop on Main Street in Great Barrington. photo: Terry Cowgill

Asked how long the tradition of student window painting in downtown Great Barrington has been going on, Monument Mountain Regional High School art teacher Neel Webber, who, is in his 23rd year at the school, shrugged. 

“I don’t know,” he said, as he watched his students paint in front of Gorham & Norton. “It’s older than Monument. I’ve heard people say that, when the high school was Searles, they were doing it. Some of these kids, their parents and their siblings have participated in this.”

Webber says he has heard — but cannot confirm — that the tradition started at the former Williams High School in Stockbridge. Williams closed in 1968 when Monument opened.

Be that as it may, the popular Halloween window-painting day puts smiles on the faces of not only the onlookers but the participants, as well.

Monument Mountain Regional High School students Jose Sagastume and Grace Phair paint in front of David Gavin Salon on Main Street in Great Barrington. Photo: Terry Cowgill

“It’s this community thing,” Webber explained. “I mean, look at the attention they get. Total strangers come up to them.” 

Of course, it’s one thing when a parent, peer or teacher compliments students on their work, Webber says, “But when some stranger comes up to them, it’s like, wow!”

“It’s a cool way to get the community involved and it also just breaks up the day, I guess,” said Monument senior Grace Phair, who was painting away with watercolors on the west side of Main Street. “It’s nice to meet people and talk to them. I mean, normally I wouldn’t even go into the David Gavin Salon.” 

“You get some people peering over your shoulders,” added Zoe Becker, also a 12th-grader at Monument who was painting on Main Street. “I had never met anyone who worked at Jane Iredale before and they’re like really lovely and welcoming. This is a really good community bonding experience, because you’re around people you’re not normally around.”

Students Zoe Becker and Tallulah King work in front of Jane Iredale on Main Street in Great Barrington. Photo: Terry Cowgill

“It’s the social interaction with the community that I like,” added Jose Sagastume, a fellow Monument senior. “Like we’ve had a couple of tourists come by asking about it and they were amazed at just the level of skill or that we can come out on even a bad day like this and that we are able to do this for the community.” 

“It’s a cool way to bring some creativity to the town,” said Tallulah King. “It’s also a nice way to showcase what you do.”

And over the years, the event has included not only art students from the Berkshire Hills Regional School District but others from some of the area’s private schools, as well. This year’s contingent included 85 students from Monument, 30 from Monument Valley Regional Middle School and 15 from the Great Barrington Rudolf Steiner School.

Sam Schroeder, who is in 10th grade at Monument Mountain Regional High School, works on his pumpkin-themed painting on Railroad Street in Great Barrington. Photo: Terry Cowgill

Most of the paintings are autumn-themed watercolors. Over on Railroad Street, 10th-grader Sam Schroeder was painting what looked to be a carved pumpkin, the stem of which was being grabbed by a skeletal hand. To the right was a puddle of pale blood.

And the unseasonably cool weather weather didn’t chill their artistic passions. Fellow sophomore Abigail Zeik was hard at work painting a woman who was being dominated by her own hair.

“Her hair is basically controlling her,” Abigail said. “I was trying to express internal demons and that’s the real scary part.” 

Webber said the event also offers all the students a sense of accomplishment by having their art chosen to be painted in downtown Great Barrington in what now has become a popular and highly competitive school-wide competition. About 200 students’ designs were entered and then judged by district art teachers to determine which of them would be painted downtown.

The event also provides artists a vehicle for showcasing their talent in a highly visible space and and gaining exposure and praise from the community at large. In contrast to the formality of school, student artists also get the chance to interact casually and positively with the public as well as with the store owners who help the students throughout the day by providing water, bathrooms, food and encouragement.

Monument Mountain Regional High School students Abigail Zeik and John Covell enjoy watercoloring on Railroad Street in Great Barrington. Photo: Terry Cowgill

The day also provides an artistic challenge to create, in the span of only a few hours, a quality mural-sized work from their original small 12-by-18-inch design.

The teachers and students said they are grateful to Steve Foley of Onyx Speciality Papers for donating the paper, Carr Hardware for providing space to set up supplies, the judges for choosing the Rotary prizewinners, and the Rotary for also supplying all the painting materials and for “creating a highly beneficial opportunity for students and adults to work together on a festive, positive community event with benefits on many levels.” 

“This event provides our students with the much needed opportunity to contribute their skills and energy to the supportive community where they live,” Webber said.

“I am always amazed how gracious the store owners are and how much praise for our students I hear from people on the street. Eighty of our students, their work, their creative process and their wonderful selves are on display for all to see for almost five hours. Sounds scary? Well, it’s not. It’s glorious.”

The judges are Rotary President Oskar Hallig, Monument alumna Alyssa Mack and a representative from the Railroad Street Youth Project. Results of the competition are posted below:

Great Barrington Rotary Club
Halloween Window Painting Contest Winners

Grand Prize Winner: 

Anika Theiman MMRHS
Window Location: Villiage Mortgage

Monument Mountain Winners:

1st Prize: Artist:   Ruby Smith         Location:  Gorman and Norton

2nd Prize: Artist: Eliza Phelp          Location: 47/RR

3rd Prize: Artist:  Simone Long          Location: Mistrals

Honorable Mention: Hannah Pigott  Location:    Lee Bank

Honorable Mention: Artist:  Sam Shroeder     Location:   Snap Shop

New Category – Political  Artist: Gracie O’Brien     Location: Fuel

Monument Valley Middle School Winners: CARR HARDWARE

1st Prize: Artist
Emily Mueller
Clementine Delsignore

2nd Prize: Artist
Athena Wingo
Evie Grossman

3rd Prize: Artist
Megan Dupont
Bridget Stephens


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