Rooted in Dade City

Building tomorrow's leaders in a community rich with tradition, character, and opportunity.

West Wing Academy strives to be an anchor for Dade City, offering families a premier educational environment where students cultivate academic mastery and exceptional character.

By breathing new life into this historic property, we are creating a sanctuary that prepares children to be conscientious citizens and proactive agents of change who uplift their community.

Our school stands as a vital resource for the neighborhood, fostering a generation of leaders committed to local service and lasting positive impact.

Steven C. Smith

Owner, Father, Entrepreneur, and Neighbor

Steven Smith brings a lifelong entrepreneurial spirit and deep commitment to community to his leadership of West Wing Academy. He launched his first business—Opening 4 Christmas tree lots—at 18 and went on to build successful partnerships with major retailers including Walmart, Costco, Sam’s Club, and BJ’s, placing beverages in more than 5,000 convenience stores and developing nutritional products focused on health and wellness.

His decision to purchase and preserve the historic church building, saving it from demolition, grew out of his love for Dade City’s “Mayberry” charm and the way neighbors still look out for one another.

The vision for West Wing Academy is also shaped by his experience as a parent: his daughters were strong, motivated students who became increasingly dissatisfied with a school experience that felt generic and not sufficiently challenging for their goals. When the rigorous, purposeful option they needed did not exist locally, their only option was to graduate early and move on to college. That story fuels Steven’s conviction that Dade City needs a high‑quality school that truly meets students where they are and helps them grow—preparing future generations for a world shaped by artificial intelligence while also honoring the enduring value of skilled trades and hands‑on work.

Rachel E. Robinson

Principal, Mom, Entrepreneur and advocate

My own school experience showed me how urgently education needs to change. I was a compliant student, but nothing in my schooling sparked real inquiry or excitement; the joy I found came from taking things apart to fix them, building, and creating art—experiences that rarely existed in classrooms at the time. My grandfather, a native Floridian and career electrician, nurtured that curiosity by teaching me practical skills like electrical work, painting, tiling, basic plumbing, and mechanics. As a parent, experienced educator, and advocate, I’ve watched the school system operate like a business, label diversity as a problem, and leave both students and teachers disengaged in a system that feels broken. My work at West Wing Academy is about changing that story—curating an environment where students experience learning rather than reading about it, discover what they enjoy and what they don’t, learn to use their individual strengths to pursue their goals and identify both their passion and proficiency.

Pursuing Doctoral Degree In School Leadership, St. Leo University
Masters Degree in Educational Leadership, St. Leo University - 2014
Founder and Owner of Illuminated Futures, LLC.
Director of Operations for an Education Services Company
Board Certified Advocate in Special Education, NASET
Former Elementary School and Middle School Administrator
Former Athletic Director and Coach

West Wing Academy was created for Dade City families who want a strong local option without having to leave their community to find an excellent school.

We are committed to offering rigorous academics, a calm and orderly learning environment, and a campus that reflects the pride our town takes in its history and future.

As we grow, we aim to be a steady partner to local families and businesses—preparing students who are well‑educated, respectful, and ready to contribute to the life of Dade City for years to come.

Community Commitment

The Future Starts Here

The Opening - August 2026

Our planned growth began in Early 2026 with purposeful renovations and improvements that reflect the standards West Wing Academy is committed to upholding from the very beginning. Every decision is guided by the child’s experience, from the design of learning spaces to the long-term development of the campus itself. At the center of this vision is a simple belief: every child deserves a high-quality educational environment that is thoughtfully designed, beautifully maintained, and intentionally shaped for daily success.

Program Expansion - 2027

In 2027–2028, West Wing Academy will expand to include 7th and 8th grade, giving more families the benefit of a single-campus experience for their children. This next step reflects our commitment to thoughtful growth that supports students, strengthens families, and contributes meaningfully to the broader community. Above is a concept rendering of a middle school math classroom.

Future Growth

As West Wing Academy looks beyond 2027–2028, our plans include a dedicated gymnasium that will allow middle school students to compete in athletics on their own campus. This gym will double as a multifunctional venue, hosting games, socials, and community events so students can enjoy both the athletic and social experiences families often seek—within a setting that reflects West Wing Academy’s standards for safety, character, and excellence.