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'One big family.' New Canaan's South school celebrates 75th anniversary with holiday sing-along event

Nearly 500 people came out to celebrate the monumental milestone Monday night.

Justin DeVellis

Dec 22, 2025, 9:29 PM

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This holiday season is extra special for one local elementary school, as New Canaan's South Elementary School celebrates 75 years in existence.

Nearly 500 people came out to celebrate the monumental milestone Monday night.

"I entered this school in kindergarten in 1952," alumni Jim Webster says. "This school was an important part of my life."

Students and their families sang holiday songs, all led by their fearless leader, longtime South school music teacher Michael Messina.

"The greatest thing about our school is that we're one big family," Messina says. "It's been that way for so many years."

Principal Matt Kascak says the landmark achievement is a testament to school staff and all those who have walked through the doors since 1950.

"This school has always had this strong feeling of family," Kascak says. "Even going back 75 years."

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