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 from historic Charlottesville. The Keswick area to the east of Charlottesville, where Oakland is located, features a number of historic homes and estates, some of which were designed by Thomas Jefferson. The country road that goes past Oakland originally was called Stagecoach Road and was one of the main thoroughfares from Richmond to Charlottesville in the 1800s.
The Oakland grounds are dominated by the pre-Revolutionary “Big House,” which served as the setting for a school for girls in the 19th century. Constructed in the mid-1700s and added on to in the mid-1800s when Oakland served as a plantation, this structure houses administrative offices and several classrooms. The school’s first dining hall was in The Big House. 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.
Historic gardens accent the main grounds. Recent efforts have brought back some of the original plant selections and a wide array of herbs have been added. 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.
The main school grounds areas are flanked by the summer camp, which was originally constructed in the early 1950s and replaced in 2007, and the year-round dormitory complex that includes the Margaret G. Shepherd Gymnasium and Recreation Center. The stone foundation of an original tobacco barn serves as the walls of Bright Leaf Terrace, an outdoor picnic and study area.
On a far 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 donkeys and our barn cats.
The grounds also consist of open fields, forests and Mechunk Creek, which traverses the woodlands area. Adjacent to the property is the historic Union Mills Church, which served as a place of worship for workers of the nearby woolen mills in the 19th century.