Recently, Dorchester County Public Schools Superintendent Jymil Thompson talked with The Cambridge Spy’s P. Ryan Anthony and WHCP Radio’s Jim Brady about the 2025-26 school year and the future. Topics included DCPS’s ranking among the state’s school systems, budget cuts and their effect, buildings slated for replacement, and the year’s successes.

The video is approximately 14 minutes long.

The children in Cierra Robinson’s Pre-K classroom learn through songs, games, and nature themes, but they also learn something else the Dorchester County teacher considers just as important: that school is a place where they are loved.

Recently named Dorchester County Public Schools’ Teacher of the Year for 2026-2027, Robinson beams when she talks about her students at Maple Elementary School. She laughs easily, tears up unexpectedly, and speaks about four- and five-year-olds with the kind of affection usually reserved for family.

“I lead with empathy,” Robinson said. “I like to get to know the child holistically. I like to know their families. I care about them more than just as a student. I learn to love them.”

That warmth helped earn Robinson recognition from school administrators who nominated her for the countywide honor. Robinson said the award still feels surreal months later.

“Every time I get recognized as teacher of the year, I get excited all over again,” she said. “It just means a lot to be recognized for something that you love so much.”

Teaching, it turns out, runs deep in the Robinson family. Robinson is the youngest of five siblings, and three of the five became teachers.

Her older sister, teaches fifth grade at Maple Elementary, while another teaches pre-kindergarten alongside her. Their mother teaches the Teaching as a Profession program at Dorchester Career and Technology Center, helping prepare high school students interested in education careers.

“They’re like my built-in best friends,” Robinson said. “Having someone so close that you can lean on in this profession is amazing.”

The conversations do not stop when school ends for the day. Robinson said family dinners often turn into brainstorming sessions about lesson plans and classroom ideas.

“We’ll be sitting there talking about, ‘Oh, that would be a great idea for a lesson,’” she said.

Robinson says she did not originally plan to become a teacher. After graduating from Cambridge-South Dorchester High School in 2015, she earned a cosmetology license through DCTC and worked full-time in a salon while attending Chesapeake College.

At first, she planned to become a therapist, hoping to help others. But during an internship, she realized she was carrying too much emotional weight from her clients’ issues home with her each day.

“I went back to the drawing board,” Robinson said. “I was sitting in my mom’s classroom, and I was like, ‘You know what? What better helping career than becoming a teacher?

She later graduated from Salisbury University in 2021 and joined Dorchester County Public Schools. This year marks her fifth year teaching.

Robinson said prekindergarten appealed to her because those early years shape how children view school for the rest of their lives. Many of her students are entering a classroom setting for the very first time.

“We’re the foundation,” Robinson said. “Building that love for school and helping them learn what it’s like to interact with other children and their teacher.”

Her classroom style is energetic and playful. Robinson sings with students, invents games, and sometimes makes up songs on the spot to hold their attention.

“If I’m bored while teaching, then they must be bored too,” she said. “So I always try to make it fun and engaging.”

She also tailors lessons to students’ personalities and interests. Robinson said she tries to understand each child individually before adapting the curriculum around what excites them.

“Building relationships is my number one goal at the beginning of the school year,” she said.

That relationship-building extends beyond the classroom walls. Robinson stays in touch with many former students and their families long after they leave her class.

“My motto is once a student, always a student,” Robinson said.

One former student who no longer attended Maple Elementary recently reunited with Robinson during a difficult time for the family. Robinson spent the day with the child at a park, took her shopping, and bought lunch.

“When she first saw me, she just cried tears of joy because she was just so happy to see me again,” Robinson said. “That impression she had will always be everlasting for me.”

Robinson said her own experiences growing up with a troubled father shaped the way she approaches students who may be struggling at home. She said those experiences help her understand children who need extra structure, patience, and encouragement.

“I can actually put myself in their shoes and give them exactly what I needed as a child,” Robinson said.

Those bonds make the final days of the school year emotional for her. Robinson said she often cries after students leave for summer break because she knows school can be a safe and stable environment for many children.

“When summertime rolls around, honestly, on the last day of school, I always have a really hard time,” she said. “I come back to my classroom, and I cry a bit.”

Even outside school hours, Robinson looks for ways to support students and families. She still cuts hair and sometimes helps students who need haircuts or grooming assistance.

“When you look good, you feel good,” Robinson said. “It’s the same thing with the students.”

Robinson credits Maple Elementary administrators and staff for creating a supportive culture that encourages creativity and collaboration. She said teachers are given flexibility to shape lessons in ways that fit their students best.

“They make time, and they’re intentional with their help and their guidance,” Robinson said of school administrators. “Here at Maple, it truly feels like a family.”

As for what comes next after being named Teacher of the Year, Robinson said she simply wants to keep growing, learning, and saying yes to new opportunities. She described herself as “a yes girl” who is always eager to try something new in the classroom.

She also hopes to continue expanding the nature theme woven throughout her classroom. Robinson said nature is something all children can connect with, regardless of background.

“Whether they’re rich or poor or wherever they come from, nature is something that we’re all familiar with,” she said.

Near the end of the interview, Robinson reflected on what she believes makes Dorchester County teachers special. She smiled as she pointed to the shape of the county itself.

“Dorchester County is shaped like a heart,” Robinson said. “I think that’s what makes Dorchester County teachers so special because they teach from the heart.”

The video is approximately 9 minutes. Editing and production: P. Ryan Anthony

Photographs: Casey O’Bier