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Chester has been at Hommocks Middle School for 14 years, teaching seventh grade for the past four years and sixth grade prior to that.
"I love the middle school students' energy level," she said. "If you don't have passion, if you don't have excitement and enthusiasm, then you are absolutely going to lose your middle school audience."
Chester's commitment to not only teaching this grade level but also influencing how subject matter is delivered to them has grown throughout her career as an educator, which she said she thinks contributed to her winning the award.
She is now vice president of the Westchester Lower Hudson Council for the Social Studies, an organization that selected her for the Outstanding Social Studies award at the local level in 2008.
"In the last couple of years, I've sort of ratcheted up my involvement in the social studies organization locally as well as in the state, so I think that, in addition to work in the classroom, is what led to the nomination," Chester said.
Additionally, she traveled to Germany and Poland last summer with the Holocaust and Human Rights Education Center.
Her most recent success, just before winning this weekend's award, was being appointed to the NYSCSS advisory panel that works on changes in the curriculum and assessments that are happening in social studies at different levels. Chester said this is one of the most enriching parts of what she does.
"I love being in class and I love teaching, but then also being able to connect other teachers who teach the same thing is great," she said. "And to have a voice in Albany about what becomes the curriculum in New York State -- that's just very important to me. It's taking the profession outside of the day-to-day work in the classroom to have an impact beyond those four walls."
On top of formal recognition from local and state organizations, Chester said that hearing from parents and students who say she has opened them up to something new is a particular honor.
"Middles school is the first time they're really seeing social studies as its own unique discipline," she said. "I think for some kids, this turns them on to the idea of like, 'Maybe I want to study history.' When I get a letter saying that someone's child decided to take AP History because of me, that always feels really good."
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