The first party of Masterton’s Small Farms Association settlers made their way up the Wairarapa valley in May 1854, arriving at the site of the township on the evening of the 21st. The township had been laid out by the surveyor W. Mein Smith, but the streets and roads so carefully delineated on Smith’s plan were simply lines on paper – there were no streets.

The settlers spent their first years breaking in their land, and establishing themselves. During this period much of their cash income was derived from working on the roads for the provincial government. By 1856 an as yet unnamed road, one chain wide, made its way through the centre of the town, partially formed and metalled. Other narrower roads were constructed to some of the nearby farms, and two ‘back lines’, later to be called Dixon and Chapel Streets, each half a chain wide, ran parallel to the main road. The first body devoted to roading in the area was the Masterton Roads Board, established in 1862. The Board received a 66 percent subsidy from the Wellington Provincial Government to help meet the costs of providing roads. The Masterton Highway Board, responsible for a similar job over a much larger area, replaced this board in 1872.