Inspired by Douglas Wilson's book, Recovering the Lost Tools of Learning, and the success of Logos School in Moscow, Idaho,* a group of homeschooling parents from Elkton, Maryland, founded Christ Classical Christian School. The doors opened in Elkton in September of 1994, under the leadership of administrator Richard Chenette and a volunteer board of directors. CCCS served twenty-one students in grades three through ten, employed two full-time staff members, and was served by several part-time and volunteer teachers and staff.

The following year, the school moved to a church location in Newark, Delaware. In 1997, the school needed more space and relocated to Hockessin, Delaware. The name was changed to Tall Oaks Classical School. The Rev. Donald Post became the school's second administrator in 2001.

At the beginning of the 2006-2007 school year, Tall Oaks Classical School moved to the Faith City Family Church building in the Christiana area of Newark. In April 2009, we were accredited by The Association of Classical and Christian Schools. The beginning of the 2010 – 2011 school year brought us to our fifth home, First Baptist Church of Delaware. In April 2011, we were reaccredited by ACCS. On June 1, 2014, we welcomed Dr. Timothy J. Dernlan in the role of headmaster after serving as principal during the 2013 – 2014 school year. Dr. Dernlan became our headmaster on June 1, 2014. During the summer of 2016, Tall Oaks Classical School relocated to the campus of Red Lion Christian Academy in Bear, DE. This move became the permanent location and home of Tall Oaks Classical School. Our new home has blessed us with sufficient space and has allowed us to continue growing.

Tall Oaks Classical School offers a Christ-centered and classical education and now serves over 200 students enrolled in kindergarten through twelfth grades. Tall Oaks Classical School employs forty-five faculty and staff.