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Fry's Spring is one of the city's largest neighborhoods with 488.64 acres, and it has an interesting and colorful history. In 1839 Nelson Barksdale gave his son-in-law James Francis Fry about 300 acres along Moore's Creek, on which Fry later constructed his mansion, Azalea Hall. The estate was famous for both architectural and landscape features, and included apple orchards, vegetable gardens, and tobacco fields. It also had two cemeteries, one for family members and one for slaves. When Captain James Archer Harris purchased it in 1875, the Azalea property had been reduced in size but the area was becoming the recreational center for Charlottesville. Shortly after Captain Harris took ownership, the County's first steeplechase was held there.

Starting around 1850, nearby Fry's Spring became popular for its beneficial waters, and a steam rail line was extended to the spring in the early 1890s (there actually were two springs, one which had iron water and one with litha water). The Jefferson Park Hotel was built in 1892 by the Jefferson Park Hotel and Land Improvement Company, which acquired a significant amount of land around Captain Harris' estate. Later an electric trolley replaced the steam train, and Fry's Spring became more of an amusement park, offering a dance pavilion, theater, and rides. The Albemarle Horse Show Association established its grounds on the site in 1905, and it was soon joined by a separate park known as Wonderland which featured exotic animals and, later, outdoor movies. The hotel burned in 1910, and was replaced by the Tudor-style Fry's Springs Beach Club, which continues to serve as a focal point for the Fry's Spring-Jefferson Park Avenue neighborhoods. A number of large homes were built around the turn of the century 1900) in the Fry's Spring/Jefferson Park Avenue area, among them White Cross on Stribling Avenue (now called Huntley Hall), the Barringer house on Valley Road, Piedmont Plantation (which extended south to Hickory Hill and east, surrounding Fry's Spring), Shamrock, the Harmon house, and the Rixey house (next to the Beta fraternity).


Captain Harris died in 1904, and his widow sold off most of the original Azalea property. After some controversy on the part of various Harris heirs regarding proper disposal of the land, the Captain's surviving daughter Zella was left with approximately 65 acres which she then sold during the 1950's and 60's. The western part of the Azalea estate became the Monte Vista subdivision (developed by Robert L. McElroy), part of the 1938 annexation by the City. The portion of Fry's Spring lying between Cherry Avenue and the City limits, including a strip of land extending to Fontaine Avenue, was part of the 1963 annexation.

Several special studies have included the Fry's Spring area: the Jefferson Park Avenue/Fontaine Avenue Neighborhood Study (submitted to the Planning and Coordination Council Task Force August 18, 1998); The City as a Park (Greg Bleam Architects, 1998); City of Charlottesville Commercial Corridor Study (Torti Gallas CHK, 2000); and From Porch Swings to Patios, An Oral History of Charlottesville's Neighborhoods.