Today we’d like to introduce you to Kathryn Cunningham.
Hi Kathryn, thanks for joining us today. We’d love for you to start by introducing yourself.
From the time I was in kindergarten, I knew I wanted to be a teacher. My mother kept one of those childhood memory books where you record each school year’s photo, friends, teacher, and future career. Year after year, I wrote “teacher.”
After graduating from the University of Texas with a degree in elementary education, I began my career in early childhood classrooms in Austin. When my husband’s career took our family to Kentucky, I shifted into directing a Parents’ Day Out program while my son and daughter were young. Once they entered elementary school, I returned to the classroom as an elementary teacher and later transitioned to the University of Kentucky, where I also completed my doctorate in educational psychology.
When we eventually moved to Winter Park, my husband and I spent a long time searching for the right place to build something of our own. We found it in Howell Branch Academy—a center with a beautiful, expansive outdoor play area shaded by towering Live Oaks. We purchased it just months before COVID shut everything down, but our remarkable teachers used that time for deep professional development, and I continued my work at Valencia College.
Before long, our waitlist grew, and it became clear that my heart—and my future—belonged fully at Howell Branch Academy. I stepped away from Valencia to devote myself to creating an exceptional early learning center. Today, I truly feel like I’m living the dream I first wrote down in that childhood memory book
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
While our journey hasn’t always been smooth, we consider ourselves incredibly fortunate. I recently attended a small business workshop through SCORE and learned that most small businesses don’t make it past the five‑year mark. That statistic really put our own path into perspective. Our passion has always been early education, but running a successful center also requires strong financial understanding—something we had to learn intentionally.
Before purchasing Howell Branch Academy, we began working with a SCORE mentor, and that guidance has been invaluable. Through mentorship, workshops, and plenty of learning from our own mistakes, we’ve grown stronger and more confident as business owners. We’ve also weathered challenges that could have easily derailed us—most notably a global pandemic and several major hurricanes. The fact that we not only survived but continued to grow through those moments is something I don’t take for granted.
Now entering our sixth year, I feel proud of how far we’ve come and grateful for the support, resilience, and good fortune that helped us get here.
Alright, so let’s switch gears a bit and talk business. What should we know?
Our early learning center is dedicated to providing an enriching, developmentally grounded education for children from six weeks to five years old, along with after‑school care for school‑age children. We specialize in bilingual immersion, and both our VPK and school‑age programs take place fully outdoors—something that is still rare in Central Florida. Families come to us because they want their children to learn through play, language, and nature, not worksheets or screens.
What truly sets us apart, though, is our team of teachers. They are the heart of our program and the reason our center feels so alive. Our teachers invest tremendous time, creativity, and energy into designing a play‑based curriculum that encourages children to explore, collaborate, and approach the world with curiosity and kindness. Their professionalism and passion shape everything we do.
Brand‑wise, we are most proud of creating a place where childhood is honored—where children spend their days outdoors, immersed in language, supported by responsive teachers, and surrounded by a community that values joy, connection, and meaningful learning. We want people to know that our programs are intentionally designed, research‑informed, and rooted in the belief that children thrive when they feel safe, engaged, and inspired.
In short, our brand reflects who we are: a warm, thoughtful, bilingual, nature‑rich early learning community committed to giving children the best possible start.
What do you like best about our city? What do you like least?
What I love most about Winter Park is the people and the thoughtful mix of businesses that give the city its character. I can spend a morning at the Farmers’ Market, enjoy lunch at a one‑of‑a‑kind restaurant, and still be home in time to take my dogs to the park or walk the trails near my neighborhood. Everywhere I go, there’s something beautiful to appreciate. That intentional planning—the way nature, community, and local business are woven together—is one of the things Winter Park does exceptionally well.
If I had to choose something I like least, it would be how the Live Oaks along the streets are trimmed. These trees are one of Winter Park’s greatest treasures, yet every few years their sweeping branches are cut back abruptly to make room for power lines. We have such stunning Live Oaks throughout the city, and I wish the trimming practices reflected their beauty and significance.
Contact Info:
- Website: https://www.howellbranchacademy.com
- Facebook: https://www.facebook.com/4605HowellBranchRoadWP/
