WESTPORT — It’s an odd feeling being told what your friends, students, coworkers, bosses and members of your community have said about you.

But just a few weeks ago, Bedford Middle School eighth grade teacher Courtney Ruggiero found herself in exactly that situation. A box of tissues was placed on the table before her as members of the state Teacher of the Year committee recounted interviews conducted over the previous days.

“It’s kind of like being at your own funeral. It was definitely a very strange, unique experience in that way,” Ruggiero remembered from her Bedford classroom during the final period of the day Monday afternoon.

The committee had been sent to Westport in late September to observe Ruggiero in front of her class and to talk to those in the community she interacts with daily to help determine whether she’d be awarded with the state’s top honor for educators, kindergarten through 12th grade.

It was announced in late August — after first receiving an anonymous nomination from a fellow teacher and completing a lengthy application process over the summer — that Ruggiero had won Teacher of the Year for her district, and in late September that she was one of four finalists in the state.

“Courtney challenges students to set aside self-doubt to reach higher and go further with every new learning opportunity,” said Bedford Middle School Principal Dr. Adam Rosen. “In my observations of her instruction, I have been impressed by the innovative and scaffolded tasks she designs, the fresh resources she continuously brings to her classes, and her universally high expectations for students.”

Ultimately, Ruggiero was not named Connecticut Teacher of the Year, but as a finalist will be involved over the course of the next year in a series of meetings with fellow educators and State Department of Education Commissioner Dianna Wentzell.

“There are quarterly meetings and I’ll get to interact with the other finalists and semifinalists. The Teacher of the Year stuff is cool but I was most excited to be involved in that sort of state level conversation and to see what people from other districts are feeling too,” Ruggiero said. “I think I’m always mindful of being sort of in a bubble in Westport and I think it’s good to hear others experiences.”

Ruggiero, who was born and grew up in Westchester County, was a history fanatic from an early age. But it wasn’t until 7th grade, when a particularly great teacher, Mr. Paul Ciancio, inspired her to follow her love of history to a career in teaching.

“Having a really good teacher I saw how you could make a career out of that,” Ruggiero said.

She attended Bates College, where she majored in history and minored in education and then got her masters in education at Brown University. After a year teaching a Fox Lane Middle School, in Bedford, N.Y., Ruggiero came to Westport in 2009. She’s taught eighth grade social studies since, and also coaches the Staples High School boys skiing team.

“It’s a great place to work. The teachers are what make it the best. We all work together with a math, science, special ed and an English teacher and they’re some of the smartest people you’ll ever meet. And they’re just so enjoyable to collaborate and be supported by,” Ruggiero said.

Ruggiero was drawn to teaching middle school, specifically, because it can be a sort of “sweet spot,” when students are beginning to form opinions and can handle intellectual discussion, but aren’t yet as jaded as some of their high school-aged peers.

“You can have good conversations with them. But they’re fun enough that you can also joke around and do things that sometimes the high school kids kind of feel like they’re over,” said Ruggiero.

Her course covers a broad swatch of American history, from American independence to present day and investigates both the positive and negative aspects of the country’s past.

“Right now they’re doing a project that goes through the Constitution, the Declaration of Independence, the failed government of the Articles of Confederation. But then we go into, P.S., we had slaves. How do we reconcile the legacy of slavery with all the wonderful things we were going to do?” Ruggiero explained.

On those, and controversial subjects from more recent history — like the most recent Presidential election, the treatment of Confederate monuments, and debates around the second amendment — Ruggiero stressed the importance of letting her students guiding the conversation.

Taking an objective stance on potentially polarizing issues is an educational ideal that Ruggiero said she’s worked toward since her days as a student, and it’s one she wrote extensively one of her Teacher of the Year applications.

“It was nice to have the feeling that the thoughts I had about education were valued,” Ruggiero said, though she noted that she believed most teachers take a similarly valuable approach.

“The only thing I don’t like about all of this Teacher of the Year stuff is that mindset of one person rising above the rest. That’s been hard to feel comfortable with,” Ruggiero said. “I’m so much a product of where I work and who I work with and who I’ve been mentored by. There are many people who could’ve gotten to this position and would’ve deserved it.”

justin.papp@scni.com; @justinjpapp1