The first white settler in Castlepoint, Thomas Guthrie, encouraged sporting evenings on the beach with the station hands taking part in athletic contests. The hands, all of whom owned their horses, also liked to bet on the relative merits of their horses, and bottles of rum were laid as wagers for the horse races along the beachfront.
As time went on these races became more organized, and picnic days were held on the beach, with horses from the whole district lining up in a series of hastily organized, and not very well documented races.
Just when the first horse races were held at Castlepoint is difficult to tell. The first hint of races is a newspaper report in 1875 reporting that a scheduled meeting at Castlepoint had not been held.
There is, however, a good record of the first organised meeting of the Whareama races, on Boxing Day 1872, and it is from this meeting that the Castlepoint Racing Club dates itself. It was held on John Morrison’s property, on what is now the Whareama domain. The hot weather was said to oppressive for the spectators, but the jockeys, whose clothing was said to be “modest in the extreme,” were well enough clad for easy recognition.
The horses obviously had great stamina. Mr Sullivans “Old Tom” won the first race, a hurdle race. The second race, a flat race held in heats was similarly won by Mr Sullivans “Old Tom.” The redoubtable “Old Tom” won both heats and the final of the staying race, meaning he started four times for four wins on the day.
The meeting was also notable for a lack of alcoholic refreshments. A report, published in the Wairarapa Standard complained bitterly about the need for a “few of the liquids which are generally included under the category of refreshments.”
There are no reports of another meeting on the site, and the next report is of the postponed Castlepoint meeting of 1875. The meeting, postponed because of the weather, might have saved the bacon of one of the attractions, as it was reported that a pig, which had been especially trained to “perfect him in the art of eluding his captors” would be unable to practice his slippery skills.
The districts sports day continued to be held at Castlepoint, on a variety of public holidays – Christmas, New Year or Easter – but as time went on, and the focal point of the district’s settlement shifted inland to Tinui, the district races also shifted westward for a time.
The first Tinui races were held near the present cemetery in 1878 although the Tinui Jockey Club was not formed until 1884. By 1887 the Tinui Jockey Club had folded, and club records indicate an attempt was made to raise an overdraft with the Bank of New Zealand to pay creditors.
The early 1890s saw a return to racing at Castlepoint and the Castlepoint Jockey Club was formed in 1891 with races usually held at Castlepoint and some events moved up the beach to Whakataki.
The Castlepoint course started in the Basin, as the main beach was bisected by the old landing shed and jetty. The horses made their way around the curve and onto the main beach. The tradition of liquor-less races had been forgotten, and the Castlepoint Accommodation House and the Whakataki Hotel both did a roaring trade, and the events were said to be very colorful.
The Castlepoint races continued throughout the 1890s until the Boer War caused the club to go into recess. The races were revived in 1906, and continued until World War One, with the last races for over twenty years held on March 7, 1914.
The club was revived, and the first official meeting was held in February 1937. The Castlepoint Cup – the day’s feature race- was won by the Castlepoint storekeeper (and habourmaster) Percy Bellis, who had also won the last cup in 1914.
The races have continued, with few exceptions, since 1937.