The Portland Academy is founded in downtown Portland.

Ruth Catlin founds Miss Catlin's School in Northwest Portland (girls, day and boarding, grades 8-12).

Miss Catlin's School moves into the newly completed main building on Culpepper Terrance.

The Portland Academy becomes The Preparatory School. Miss Priscilla Gabel is a teacher.

Hillside School building, grades K-8 coeducational, is completed on Culpepper Terrace.

The Cady School of Music dissolves and many students transfer to Hillside School.

Ruth Catlin deeds the School to the Board of Trustees, which incorporates The Catlin Hillside School.

The Preparatory School becomes Miss Gabel's School.

Miss Gabel's School moves to Raleigh Hills and becomes Gabel Country Day School.

The Catlin Hillside School discontinues its boarding component.

Gabel Country Day School discontinues the high school, continuing classes for grades K-8.

The Catlin Hillside School and Gabel Country Day School merge to become The Catlin Gabel School.

The Catlin Gabel School uses both campuses, enrolling the first coeducational high school class on Culpepper Terrace, but losing the Gabel property to Raleigh Park Public Schools.

Catlin Gabel purchases the Dants' Honey Hollow Farm and relocates the Upper School there in the fall. The Dant House, Barn, and Paddock serve about 70 students.

Grades K-8 move to the Honey Hollow campus.

The Catlin Gabel School now enrolls 700 students, preschool-12th grade. The Dant House remains the heart of the Upper School; the Barn and Paddock are common areas for all students.