The Grounds

A unique and ideal setting for learning and character development, Oakland School is located on a 450-acre property in a peaceful country setting 10 miles east of Charlottesville. The area features a number of historic homes and estates, including the University of Virginia and Thomas Jefferson’s estate, Monticello. 

Maintaining and preserving Oakland’s open space setting is a top priority for the Board of Directors. This commitment ensures that all will be able to enjoy and benefit from the historic campus for generations to come.

Oakland School students walk across part of the 450-acre campus.
The Big House is not only a historical symbol for Oakland School, but also a space for offices and classrooms.

The Big house

The Oakland grounds are dominated by the pre-revolutionary “Big House,” which was a girls school in the 19th century. Constructed in the mid-1700s and added on to in the mid-1800s when Oakland was a plantation, this structure houses administrative offices and several classrooms. The school’s first dining room was in the Big House. 

The Old Kitchen has been at Oakland School since the very beginning.

the school house and old kitchen

Behind the Big House are a series of school buildings including the Old Kitchen, which was just a chimney when Mrs. Shepherd first set foot on Oakland Farm in 1922, and the School House built in 1963. The village-like design allows everyone to see and greet one another as they walk to and from their classes.

Students tend to and learn from the historic gardens at Oakland.

historic gardens

Historic gardens accent the main grounds and feature some of the original plant selections and a wide array of herbs. A gazebo, built in honor of Joanne and “Pep” Dondero, longtime stewards of the farm and school, houses a swing that is an idyllic spot for reading.

Hillside House in the summertime.

Hillside house

Aptly named, this two-story building is nestled into one of Oakland’s sloping ridges and is where students spend most of their academic day. The Hillside House is central and contains a number of classrooms where children receive reading, writing, math, and science instruction in intimate classes.

Two Oakland School students practice yoga in the dorms.

Summer cabins and dormitories

The main school grounds areas are flanked by the summer camp, which was originally constructed in the early 1950s and updated in 2007, and the year-round dormitory complex that includes the Margaret G. Shepherd Gymnasium and Recreation Center.

Oakland School students take advantage of the Equestrian Center.

Equestrian Center

On a corner of the property is the stable complex and riding ring. The more than 16 equine residents of Oakland are very well cared for and students take part in this process to learn responsibility. Other much-loved residents of the barn are our barn cats and donkey.

The historic Union Mills Road runs right past Oakland School.

union mills road

Originally called Stagecoach Road, the country road that goes past Oakland was one of the main thoroughfares from Richmond to Charlottesville in the 1800s.

Union Mills Church in summertime, surrounded by nature..

union mills church

Adjacent to the property is the historic Union Mills Church, which was a place of worship for workers of the nearby woolen mills in the 19th century.

Oakland student explores campus near a log cabin.

Places to Wander

The grounds also consist of open fields, forests, and Mechunk Creek, which traverses the woodlands area.