Ploughing matches were a part of the Shoalhaven area throughout the 1860’s, 70’s and 80’s. Following the election of a committee from a public meeting on 4 June 1886, one such match took place in Ulladulla on the property of TR Kendall known as ‘Whopindilly’. The ploughing occupied the morning and in the afternoon a shooting match was held.
A meeting of the committee was held on 5 November 1886, where it was decided to hold an exhibition of livestock, dairy produce and other farm products on the property of Mr W Martin at East Milton. So successful was this event, the committee resolved that it be made an annual event. Owing to drought and bushfires, there was no Show in 1867, but the ploughing match of the following year attracted 300 spectators. The Show continued to grow as the population of Ulladulla rose to 2000, and with the opening of the telegraph office on 15 June 1875, the southern isolation was greatly reduced.
The Show was dogged by bad luck. In 1870 floods caused havoc. The Show of 1888 went ahead without cattle because of an outbreak of pleuropneumonia. In 1899 continued dry weather and depression in the dairy industry forced the Show to be abandoned. The Show of 1905 was abandoned due to fires sweeping the Milton district.
However over this time, local MP Captain Millard secured a grant of 150 pounds to the purchase of 16 acres of John Ingold’s farm opposite the central butter factory and included a cricket ground as a site for new showground.
In 1922 the name of Ulladulla A&H Society was changed to Milton Agricultural and Horticultural Society to more properly identify the farming and dairying nature of the district.