Highland was founded in 1928 by Dorothy Rust and Lavinia Hamilton as the Warrenton Branch of the Calvert School of Baltimore.

As stated in its mission, "Highland School prepares students to thrive, lead and serve in a diverse and dynamic world, developing essential skills and character by challenging them with a demanding academic and co-curricular program."

A Humanities and Instructional Technology wing for the Upper School was completed during the fall 2009.

A new turf stadium, softball field, and outdoor courtyard were also completed in 2009.

Advanced Placement courses are offered to Upper School students, beginning in their sophomore year.