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mayor Peter Marchetti with first-prize winner Kayleigh Capitanio and her father on Wednesday at City Hall. Capitanio's artwork will be the poster for this year's Pittsfield CityJazz Festival.
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Marchetti with third-place winner Maso Casucci and his mother.
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Berkshires Jazz President Edward Bride holds up the jazz festival poster with Capitanio's artwork.
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Winning artworks: Capitanio, left, Sara Sofia Plazas Cortez (who did not attend) and Casucci.
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Marchetti and Bride with Pittsfield High art teachers and the winners.
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The artwork is on display on the first floor of Pittsfield City Hall.
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Pittsfield Celebrates Jazz Art Contest Winners

By Brittany PolitoiBerkshires Staff
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Mayor Marchetti with contest winners Maso Casucci and Kayleigh Capitanio. 

PITTSFIELD, Mass. — For the month of April, Pittsfield High School students' jazz-inspired works bring color and design to the corridors of City Hall.

Kayleigh Capitanio secured the first-place award for the Berkshires Jazz Student Art Contest with a vibrant work depicting a guitar, piano, and music notes. The piece was created in art teacher Lisa Ostellino's classroom while listening to the music that inspired it.

"I didn't think that idea was going to be good until I started drawing," Capitanio explained. "And then I think what really helped was that we were listening to jazz music and it just got me in the groove, I guess."

Each year, Berkshire Jazz Inc. sponsors the student art contest to engage the community. The winning entry becomes the graphic for the Pittsfield CityJazz Festival, which kicks off on April 24 and runs for 11 days.

"These are all over Berkshire County now, so you're famous, at least locally, soon internationally," Berkshires Jazz President Edward Bride said to the winner, noting that Pittsfield Community Television was recording the award.

Sara Sofia Plazas Cortez came in second with a black-and-white drawing of musical instruments and musicians, and Maso Casucci was voted third place for his warm-toned work, which included a curved piano and fretboard.

"I really like the colors," Casucci explained, adding that a drawing of a person singing was painted over in the bottom right corner, making that portion abstract.

"Every single one usually has a piano. I wanted to include guitar because I play guitar, so I thought that was a cool addition to it."

Mayor Peter Marchetti said it is "fantastic" to see when he comes out of his office.

"I've spent quite a bit of time, I think this year, in both art classrooms as I was making some rounds in PHS, and it's quite an energized group of folks," he said.


"So I'm happy to be able to present the awards to the winners."

The artwork will be displayed in City Hall for the duration of National Jazz Appreciation Month, an initiative of the Smithsonian Institution that was sanctioned by Congress in 2001. The Student Art Contest was created by Berkshires Jazz board member Art Niedeck nearly two decades ago.

PHS has participated for 16 years, overseen by art teachers Colleen Quinn with support from colleagues Ostellino, Michael Greenberg, and Alisa Mierzejewski. Small cash prizes are awarded to the top three works.

"I like what they do in class to be relevant to the community," Ostellino said.

"Jazz is alive in Pittsfield. I keep stressing that, and this is also where I like to try to explain some career options for them, so graphic arts, things that they're doing in class are very relevant to what happens outside in the world."

This year, the contest was judged by Karen Carmean, Erin Murphy, and Carolyn Newberger. Murphy, a graphic designer, said the winning drawing was bright and dynamic and works well as a poster.

The 19th annual Pittsfield CityJazz Festival kicks off with an open jam session on Thursday, April 24, and the 11-day fest includes free and ticketed events, including the "jazz crawl," jazz brunches, the jazz prodigy concert, and headline concerts featuring Dawning Holmes and the Legendary Count Basie Orchestra.  

Bridge pointed out that Berkshires Jazz All Star Youth Ensemble will open for the orchestra at the Colonial Theatre on May 3

"It's a tradition that's long-standing and we all look forward to that part of it," he said. "It's another way of integrating the youth into the jazz scene."


Tags: art contest,   jazz,   PHS,   

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Pittsfield Schools See Better Building Utilization, Continued Choice Outs

By Brittany PolitoiBerkshires Staff

PITTSFIELD, Mass. — Students return to school in two weeks; Pittsfield will have one less elementary school and around 100 fewer students. 

The School Committee was updated on enrollment for the 2026-2027 academic year during last week's regular meeting. 

At this time, the Pittsfield Public Schools had 4,586 students, compared to 4,682 at the end of the 2025-2026 school year. Superintendent Latifah Phillips said this has been the district's trend for years and is not surprising. 

"Across all of these grade levels, we have a decrease. I believe of about 80-90 students. I think it's at eighth grade that we're going to look into and make sure that our data is accurate," she said to the School Committee last week. 

"But otherwise, the enrollment is following the trends that we have expected in probably the last decade." 

With this school year comes the closure of Morningside Community School and the middle school restructuring that sends Grades 5-6 to Herberg Middle School and Grades 7-8 to Reid Middle School. 

Fifth grade enrollment was subtracted from last year's elementary enrollment, and these reflect the reassignment of Morningside students to Allendale, Capeless, Egremont, and Williams. 

Phillips pointed out that this process has increased the use of school buildings, as underutilized buildings were one of the concerns that led to institutional changes. 

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