In 1859 horse racing was held on a rough bush track and the Melbourne Hunt Club held occasional meetings in Caulfield. A racecourse was laid out on the site where the Hunt Club kennel was kept. In 1876 the Victorian Amateur Turf Club was formed and obtained the site for its metropolitan race course. The first Caulfield Cup was run in 1879.
Land survey maps for the Caulfield district were published in 1853, and the first sale of Crown allotments was in 1854. The Caulfield Roads District was proclaimed in 1857. In 1860 a shirt-lived school was established by four church congregations, and in 1864 a school was opened which became the Caulfield primary school. In 1865 the population of the district was estimated at 508.
The 1870s saw considerable development of Caulfield. The Roads District became a shire on 17 April, 1871, and the Caulfield railway station was built in 1879 as part of the South Yarra to Oakleigh to Gippsland line. Two years later the Caulfield to Mordialloc line was opened. While this construction activity was under way an entrepreneur William Ross proposed the building of another line across the south of Caulfield shire, from Oakleigh to Elsternwick. It was associated with the Ross sugar beet factory, using sugar beet grown in Gippsland. The line did not open until the late 1880s, but failed during the depression in the following decade. Its route is traceable on present-day street maps along Oakleigh Road and a linear park which is a prolongation of the road.
Caulfield in 1882 was a market-gardening district with about 182 ha. of orchards with three churches, two hotels and the racecourse. By the end of the decade it was described in the Victorian Municipal Directory as a leading suburb with residences that had been rapidly built. There were six churches and several private schools, a municipal hall and offices, and tram routes from Elsternwick to the Caulfield and Glenhuntly railway stations. On 4 May, 1901, the district's urbanisation was acknowledged by the shire becoming a borough, which became a town on 26 September of that year. The Caulfield municipality acquired separate suburbs, and the Caulfield township was in the north. The northern municipal boundary followed Dandenong Road, and the railway station and racecourse were quite close to it.
Melbourne's urban expansion as it affected the Caulfield municipality was begun on the western side well before the turn of the century and concluded on the eastern side where it adjoined Oakleigh in the late 1930s. The period of most rapid growth was from 1900 to 1920, and the Caulfield township was somewhat early in that period with its proximity to public transport facilities. Councillor (Sir) Frederick Eggleston was a councillor from 1911 to 1920, and a pioneer supporter of town planning. On 26 May, 1913, Caulfield town council became a city. In the following year Caulfield Central School was opened, and in 1922 the Caulfield Technical School was opened as a regional facility convenient to Oakleigh and Mordialloc. (In 1958 it became a Technical College, nine years later the Institute of Technology and finally the Caulfield campus of Monash University.)
Caulfield's northern boundary is just south of an escarpment more or less followed by Dandenong Road. North of the escarpment is hilly, more elevated land than the land on which the municipality is situated. There were several swamps in Caulfield, one being just west of the racecourse and the low-lying land was blamed for water-borne diseases. Sewering was a major concern in the 1890s, to replace cess pits, along with water reticulation. By 1914 reticulated water was available on most new housing estates. Several swampy or low-lying areas became parklands. Paddy's Swamp from which peat and sand were extracted in the 1860s and 1870s, became Caulfield Park, the main sports area in Caulfield near the racecourse. On 16 April, 1913, the part of Caulfield municipality between Poath and Warrigal Roads was annexed to Oakleigh borough.
Caulfield is shown in street directories as consisting of Caulfield North and Caulfield South (each distinct postcodes) and a minuscule Caulfield East around the railway station and included in the Caulfield North post code. Caulfield East includes the Monash University campus (former Institute of Technology), a shopping centre and a reserve. Caulfield North contains the racecourse and the Victorian Racing museum, the Arts Centre alongside the Town Hall, Caulfield Park, a strip shopping centre at Balaclava and Hawthorn Roads and private schools - Shelford Anglican Girls' School (1898), and an Anglican Boys' Grammar School, Grimwade House (1918). Near Grimwade House are two Synagogues catering for the substantial Jewish population in St. Kilda East and west Caulfield. In the same area is a boom-time mansion "Labassa", which has become National Trust Property. Caulfield High School, near the racecourse, was opened in 1960.
Caulfield South has a large general hospital which has grown from a first world war military hospital which was put in the "Glen Eira" mansion. Bisecting the area is the Glenhuntly Road tramline and shopping strip. Important open spaces are Princes Park (with four ovals, tennis and bowling facilities) and a linear park along the former Rosstown railway. The Brighton Cemetery is also in Caulfield South, having been established in 1849 before the Roads District was defined.
Caulfield municipality included Carnegie, Glenhuntly, Murrumbeena, Ormond and Ripponlea.
In 1987 the median house prices for Caulfield North and Caulfield South were 104% and 61% respectively above the median price for metropolitan Melbourne. Much the same margins were recorded for the next ten years.
Caulfield city was united with part of Moorabbin city on 15 December, 1994, to form Glen Eira City. Its census populations were 15,919 (1911), 65,297 (1933), 81,865 (1971) and 67,776 (1991). In 1911 the Caulfield township had a census population of 7,669.
Murray, Peter R. and Wells, John C., "From sand, swamp and heath . . . A History of Caulfield", City of Caulfield, 1980.
Solomon, Geulah, "Caulfield's Heritage" (4 vols.), City of Caulfield, 1989.
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