Classes for the children of German immigrants in the Cherry Spring community were held in homes until 1885. At that time, a 31' x 23' schoolhouse was built using locally quarried limestone on land donated by H. Bratherich. On dedication day, students marched in a parade from the home where classes had been held to the new building. Cherry Spring, District #16, added a large pavilion in 1936, despite the Great Depression. The stage area had moveable walls, which allowed it to be used as a second classroom. Grades one through five met in the "Little Room" on the stage, while grades six through nine met in the original rock building, or "Big Room."

In the early days, students walked, rode bicycles, or came by horseback. Saddles were stored in the "Saddle shed"; the horses were tied to stand and wait for school to be dismissed. One student, in the 1920's, even rode a donkey. Like clockwork, at 11:45 almost every morning, the donkey would bray, dismissing everyone for lunch.

Other notes of interest are the student enrollment and the teachers' salaries. In 1903, with a student enrollment of 41, the teacher's salary was $35. With 53 students in 1910, the teacher made $50. In 1920, the teacher's salary was $82.50 and 48 students attended. Until the 1950's, teachers would often board with residents of the community.

Each May, school closing celebrations were anticipated by the entire community. While visiting with neighbors and other acquaintances, attendees were entertained with oompah music, plays, and baseball games. Hundreds of pounds of barbecue were prepared on the large open pit to feed the crowds.

The Cherry Spring School served the community residents until 1962, when it was consolidated with Fredericksburg ISD. During the 76 years school was held at Cherry Spring, almost 400 students and 42 teachers passed through the doors. Today, the school is a landmark of early education in Gillespie County. On May 11, 1990, a state historical marker was placed on the rock school building.

The Cherry Spring Community Club now regularly uses the schoolhouse and pavilion for their meetings, and playing games of "42", on the second Friday of each month. On the second Saturday in September, club members, families, and friends also hold a barbecue picnic.