Windsor Elementary’s Wooley equips students to navigate life

Published 5:48 pm Friday, January 6, 2023

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Courtney Wooley grew up knowing that she wanted to be a teacher, and now in her eighth year in that profession, she has been recognized as the very best that Isle of Wight County Schools has to offer.

Wooley is a special education teacher at Windsor Elementary School, and she was recently named that school’s Teacher of the Year, the school division’s Elementary Teacher of the Year and the IWCS divisionwide Teacher of the Year.

“I am just so incredibly grateful,” she said.

She noted that she is grateful she gets to shine a spotlight on the amazing things that can happen in special education, and she particularly took joy in highlighting her students.

“Anyone who comes into my classroom can see that we just have a really amazing group of students who work so hard,” she said. “And really, a lot of magic happens in here, and it’s a very safe, comfortable place for anyone to come in and just be who they are. And I love working with them and giving them the tools that they need to go out into other areas of the school and have inclusive experiences with their peers.”


Wooley was born and raised in Isle of Wight County and had a distinct passion for education from a young age.

“I grew up knowing that I wanted to be a teacher,” she said. “So my earliest memories were setting up my stuffed animals, setting up friends — whoever would participate with me — and conducting little classes and teaching little classes and just kind of playing school.”

She said she has papers from when she was in first grade that read, “I want to be a teacher when I grow up.”

“So it’s something I’ve always wanted to do since I can remember,” she said.

“Growing up, I was a student in Isle of Wight County Schools, all through elementary, middle and high school, and I remember in middle school, I would be in class, and we would have students come from a special education class to sit in with us for different subjects,” she said. “And they would come in with an assistant, and I was always very interested in the students and getting to know them as people and kind of getting to know what their school day looked like.

“So that’s where I got my first taste of what special education was as far as ‘self-contained’ — the type of special education that I teach,” she added.

She explained that self-contained special education creates a situation whereby students are normally in one setting for most of the day — in this case, her classroom — but might push out into other classes for some of their day. They also join with students in other situations, like for meals in the cafeteria.

Wooley recalled that once she moved up to high school, she got a job working at a daycare and found herself gravitating toward the students at the daycare who seemed to need more support to function in that setting than their peers did.

“And then also, I was in the Teacher Cadet program at Smithfield High School, so I went out to schools in Isle of Wight County, and I kind of shadowed different teachers and got to practice planning and implementing lessons while I was in high school, and in that experience also I just felt a pull to work with students who needed a little bit more support than their peers,” she said.

An IWCS news release noted that she was a 2009 graduate of Smithfield High. She then earned her undergraduate degree in interdisciplinary liberal studies and exceptional education from James Madison University and her master’s degree in special education from Old Dominion University.

Then, for one year she was an English as a Second Language tutor in Hampton, and after that, she worked for six years as a special education teacher for Hampton City Schools before coming to teach for IWCS.

In the IWCS release, she was praised as being “passionate about helping her students develop their unique gifts and giving them meaningful and intentional inclusive experiences with their peers.”

Wooley will serve as the school division’s representative in the Virginia Teacher of the Year program, according to the release.


Wooley, who lives in Isle of Wight with her husband and two sons, shed light on what fuels her passion for teaching in special education.

“I just love getting to get to know students that communicate in a different way,” she said. “So all of my students are placed with me because they need support with academics, they need support with communication skills and with behavior skills, so I get students who communicate in a non-traditional way, whether that be sign language or a communication device or just language that sounds a little bit different than their peers. I get to kind of know each of them in their own little language, and it’s truly incredible to watch students learn how to navigate the world and learn how to be a part of the community.

“And getting to work with students and helping them grow their communication and watching those communication skills flourish is really amazing,” she said.