Chesterton Academy of Milwaukee

08/29/2026

Retreat Day #2!!

Our second day at the Catholic Ecology Center began with Holy Mass and was followed by our first field day activities of the year, including volleyball, crossnet, canoeing, and cross country. All students demonstrated healthy competition and good sportsmanship, as well as the Chestertonian joy that is so essential to our school.

We look forward to seeing you all next week!

08/28/2026

Today we celebrate the Feast of St. Monica, a mother whose perseverance in prayer continues to inspire the Church centuries later.

For years, St. Monica prayed faithfully for the conversion of her son Augustine, trusting in God even when she could not yet see the fruits of those prayers. Her steadfast love reminds us of the profound influence of parents and of the power of faithfully entrusting those we love to God.

At Chesterton Academy of The Holy Family, we are especially grateful for the parents who make countless sacrifices, offer countless prayers, and work alongside us in the formation of their children. St. Monica reminds us that this work of formation is ultimately entrusted to God and His grace.

May we never underestimate what God can accomplish through a faithful parent and a persevering prayer.

St. Monica, pray for us!

08/28/2026

Please join us in praying for our students as they begin a new academic year!

Today, our students kicked off the school year with their annual back-to-school retreat. They began the day by sorting new students into their respective houses, then loaded up the buses and headed to the Catholic Ecology Center for a full day of activity! The main event involved each house designing and racing its own chariot, followed by canoeing and hiking, and ending with a Eucharistic procession and adoration.

Check back tomorrow for more updates on what our students are doing in these first days of school!

08/26/2026

Our freshmen have officially begun their Chesterton journey! 📚🍎

Today, our class of 2030 started the school year with freshman orientation. They began the day with assembly and daily mass, spent time getting to know the faculty and their new classmates, learned about what defines a Chesterton student, and concluded with evening prayer in the chapel. Can’t wait to see all of you tomorrow!

08/26/2026

Classical Catholic art isn't just decoration. it's a window into the divine. Sacred art elevates the human soul, helping us contemplate God's truth and goodness through visual beauty.

08/26/2026

In a classical Catholic education, we don't just teach students what to think, we teach them how to think.

Through the Socratic Method, learning begins with meaningful questions that spark genuine inquiry.

Instead of passively absorbing lectures, our students engage in rich dialogue, wrestling with ideas and discovering truth for themselves.

Learn more about our classical curriculum at the link in our bio!

08/26/2026

Christopher Nolan’s The Odyssey has millions of adults talking about Homer again.

In her new article for Forbes, Emily de Rotstein, Executive Director of the Society of G.K. Chesterton, explores what this renewed interest says about our hunger for lifelong learning—and how classical education can extend well beyond the classroom to shape entire families.

Read “Why Nolan’s “Odyssey" Is Inspiring Adults to Learn Again": https://bit.ly/4gef7Sx

08/26/2026

07/13/2026

Freedom is one of the greatest gifts we possess.

But freedom is not simply the ability to do whatever we want. Authentic freedom is the ability to choose what is true, good, and beautiful.

This is why formation matters.

Through daily habits, virtue, prayer, friendship, and the pursuit of truth, young men and women learn to use their freedom well—not merely for themselves, but for the service of God and others.

07/13/2026