In 1881, Mr James Campbell who became the founding President, called a public meeting to consider forming a local Agricultural and Horticultural Show Society. It took almost four years before the first show was staged in 1885, which was a great success. Even a boxing troupe had rented space in the early 1930s. With the banging of the base drum people were invited from the crowd to go a round or two for a pound or two.

There were three breeds of cattle exhibited at the first show. There were many successful local exhibitors. Following the war motor transport became available and outside exhibitors made the competition very strong. In the 1980s the Cochrane family showed both Illawarra and Jersey cattle, breeding Sydney Royal Show champions in both breeds.

As the years progressed, more and more horse events were included in the district Show programs with displays of horsemanship thrilling the visitors. A Kangaroo Valley A. & H. Turf Club was implemented in late 1956 to hold race meetings three times annually: New Years Day weekend, the Saturday nearest Anzac Day and the Six-hour Day weekend. The last recorded races took place on 17 November, 1962.

The first, second and third Shows were on a piece of land on the bank of the river at the rear of what was then known as the Commercial Hotel, now the Friendly Inn. The livestock exhibits were paraded on this land while the fruit, farm produce, etc. were exhibited in the Church of England School Hall.

The fourth show was moved to land, with a 10 year lease from the Alex Osborne Estate, and situated at the east end of the village almost opposite the to the cemetery. Then a further 15 year lease was gained. Improvements were made in the form of cattle yards, horse stalls and a show pavilion. Most of the buildings erected were transferred to Osborne Park Showground. The pavilion as it stands today is substantially the same as the original structure.

In the following years, electrical power in 1947 was installed as well as a town water supply which bought about cultural changes in the Valley.

After much planning and discussion work started in March 1953 to level the recreation ground, next to the School of Arts, to make a showground and sports oval. H. O. Cox was Chairman of the Works Committee to co-ordinate the move and oversee the finances, while he was still Chairman of the A. & H. Association. Men and women alike worked voluntarily to make sure everything was ready for the 1956 show including the oval fence of 184 posts and 182 panels. Mr. H. O. Cox obtained the deeds of the old showground and it was found that all the Trustees named on the deeds were deceased. Three new Trustees were appointed: H. O. Cox, A.R. Chittick and L. W. Vance and the ground was subsequently sold for 690 pounds.

Once work was completed the Kangaroo Valley A. & H. Association relocated the showground to its present site at Osborne Park and the first show did go ahead 1956. Unfortunately, there was a huge downpour on this day but all who attended enjoyed themselves.

Apart from the cattle and the horses, the major attraction over the years at the Show is the general pavilion followed closely by the poultry pavilion. The Show Committee researches each show to see how the pavilion may be improved and a great deal of thought goes into arranging the exhibits.

In 1970 the A. & H. Association Ladies’ Auxiliary was formed catering for Show luncheon, Dinner Dance and the Debutante Ball which raised funds which were very helpful to the A. & H.