The southern Wairarapa was one of the earliest settled parts of the North Island, owing to the fact that much of it was without bush, or covered in light bush and scrub, at the time of European settlement during the 1840s. Some of the first travellers in the district described it, perhaps misleadingly, as a grassy open plain; but whatever the precise vegetational character of the region, it was sufficiently open to permit swift and easy penetration by the graziers. Consequently, large areas of the plain and of the eastern coastal districts were subdivided into relatively large stations, many of which have remained, in name at least, until the present day. On the western edge of the plain, at the foot of and parallel with the Rimutaka Range, lay an extent of bush country which was exploited by the settlement associations that were responsible for the establishment of the boroughs of Featherston, Greytown, Carterton, and Masterton. Despite the barrier to communications presented by the Rimutaka Range, a road link with Wellington was established by 1859, and Masterton was joined to the port by rail before 1885. Many of the sheep stations maintained communications by coastal shipping, Whareama, Castlepoint, and Akitio being three of the principal loading points. A road between Castlepoint and Masterton was formed by 1880–81. Thus, despite the isolation of the eastern hill country, the swampy nature of the lower Wairarapa, and the difficulties of communication with Wellington, the rural population had reached by the census of 1886 a total figure of 7,930.

A completely contrasting situation existed to the north of Masterton, in the northern Wairarapa or Forty Mile Bush, where the dense bush cover had so restrained settlement that the total rural population at the 1886 census numbered approximately 1,650. The commencement of the clearing of the bush is usually dated by the settlement at Mauriceville in 1873, but the settlement of the Forty Mile Bush was not completed until the turn of the century when the railway line from Wellington to the southern Wairarapa was linked with the Hawke's Bay line at the Manawatu Gorge. The bush was settled largely by men with limited capital, members of settlement associations, often Government sponsored. Consequently, the distinction between the northern and southern parts of the Wairarapa arising out of the differing vegetational character was emphasised further by social and economic factors. Even to the present decade the southern Wairarapa has managed to identify itself socially with the early period of the run holders, whereas the northern Wairarapa has never lost the anonymous character of its early settlement. Many of the original run names are preserved, White Rock (1844), Waitaranga (1846), Flat Point (c. 1851), as are the names of the early run holders, Bidwill, Gillies, McMaster, Riddiford, and Tiffen. Apart from the four towns of Masterton, Carterton, Greytown, and Featherston, all named after men prominent in the affairs and politics of the Wellington Province (Martinborough, c. 1879, is a later foundation), there are few other nucleated settlements. In the Forty Mile Bush villages are numerous, but only the name Ballance (Prime Minister, 1891–93) gives any indication of the period of settlement. All the villages were laid out on a rectangular pattern, the land subdivided into units of 40 acres or less, the farms lying adjacent to the small commercial and artisan centre. Very little of the original property or village pattern persists. The properties have been enlarged to 100 or more acres in the western dairying areas, or to 1,000 acres in the eastern store-sheep hill country which was quite unsuited to the preservation of the small scale farming. The Alfredton area provides an excellent example. Some villages have retained a few services, a shop, school, church, and dairy factory – Mauriceville, Nireaha, and Mangatainoka. The majority of villages now give little indication that once they contained 200 or 300 persons. Mauriceville West is perhaps the most moving case; the remainder are no more than place names.