[Recap] Chesterton Gala 2023

May 9, 2023

Chesterton Academy of Orlando

Chesterton Academy was delighted to host our first annual Gala Dinner on Saturday, May 6, 2023 at the splendid Orlando Marriott World Center (which, as we learned from our keynote speaker, is the largest Marriott hotel in the world!)

It was a spectacular night, full of beauty and hope. We initially planned for around 200 guests but nearly 450 people registered for the event!

Emcee Daniel Boyd guided the night and first introduced Brandon Vogt, our founder and chairman, who offered a "State of the Academy" address. (Read his entire talk here.)

Brandon spoke about the two great crises facing young people today—education and evangelization—and how Chesterton Academy's twin pillars, classical and Catholic, directly answer those challenges. He also revealed how the school plans to expand in the future, from enrollment (doubling from 30 students to 60 next year) to the campus (building a new chapel and science lab) to its culture of faith (new spiritual events and experiences for the students).

The Chesterton Academy student choir then performed, singing a resplendent Latin hymn by St. Thomas Aquinas (“Adoro Te Devote”) before unveiling, for the first time, the Chesterton Academy alma mater, composed by our own choir director, Cristian Caiola. Tears welled up around the room at the beauty of their voices.

The choir was followed by three testimonies. Sophomore students Sophia Bracero and Strummer Klein each shared how Chesterton Academy has transformed their lives. Nathan and Anna Bond, co-founders of Rifle Paper Company, explained why they support the mission of Chesterton and what led them to purchase the campus now used by the school.

Our keynote speaker, Dale Ahlquist, then spoke about why he co-founded the original Chesterton Academy in Minneapolis back in 2008. Mixing wit, humor, and profundity, he affirmed the value of classical education in shaping the whole person, producing young men and women full of wisdom, virtue, and faith.

Jim Dempsey, friend of the school, then walked through how to become partners in this great mission. He explained our target need for the night was $265,000, which would allow us to continue all the good things we're doing and more. However, he also introduced three special projects:

  • An expanded chapel ($20,000)
  • A new science lab ($11,000)
  • A year's worth of life-changing events ($12,000)

Those three projects would accelerate the school to the next level and brought the total goal for the evening to $308,000.

By the grace of God, we are thrilled to announce that the total raised that night in gifts and pledges exceeded $365,000, allowing us to accomplish all those goals and more!

We are beyond grateful to God. The Lord has blessed this high school in so many concrete ways, and the Gala evening was just the latest instance of his Provident care.

Once the night drew to a close, we immediately began planning for next year's Gala Dinner! We encourage you to place the date on your calendar: the 2024 Chesterton Academy Gala will take place on Saturday, April 27, 2024.

We hope to see you then!


Thanks to Victora Ybarra Photography for these wonderful photos!

Chesterton Academy of Orlando


Chesterton Academy of Orlando is a classical high school, grounded in the Catholic faith. Our mission is to help students recognize the true, imitate the good, and adore the beautiful, falling in love with the source of it all—God himself.

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