The purchase of Churchill Fields Park in 1927 began as the part of a special scheme. Following the First World War, the McKittrick Company had tried to profit from buying and then selling a lot of real estate in the yet undeveloped Westdale area. They had went so far as to build a bridge, plan sub-divisions and sewers, and begin discussions with McMaster University about moving to Hamilton from Toronto. All these things were done in hopes of improving the price and prestige of their properties.
However, because of an economic recession during the post-war period, the McKittrick Company made much less profit than they had planned. They went into debt to the city for unpaid taxes, mortgages, bridge and sewer charges. To help save the company from complete bankruptcy, the City Council voted to buy their land for a very good price, $200,000 ($1,000/acre, excluding the water lots). The 152.57 hectares (377 acres) of excellent land consisted of 53.83 hectares (133 acres) of water lots, 52.61 hectares (130 acres) of hillside, and 46.14 hectares (114 acres) of level land ideal for sports. In the transaction, no money actually changed hands, but a part of the McKittrick Company's debts, including $134,000 to the City, were cancelled.
The city's decision to buy the land, and turn it into Westdale Park actually improved the value of the surrounding lands even further. As a result, after only a couple years, the first building boom in the Westdale area began.
In 1945, during World War II, on the suggestion of T. B. McQuesten three leaders of the British empire were honoured, when Hamilton parks were named after them. Westdale Park was renamed Churchill Park after Sir Winston Churchill (1874-1965), the prime minister of England from 1940 to 1945. The two other leaders honoured were General Henry Duncan Graham Crerar and Field Marshal Viscount Montgomery of Alamein.
The Churchill Fields Bowling Club opened its first lawn bowling green in May 1958, and a second in the summer of 1960. A clubhouse for 200 people by architect Stanley Roscoe was built December 1958 to August 1959. The building was finished late, because of a serious fire on the construction site in June 1959.
Churchill Park actually belongs to the Royal Botanical Gardens, but the City has been allowed full use of it since May 24, 1966.
In June 1996, the City took over the Teaching Gardens (sometimes called the Children's Gardens) from the Royal Botanical Gardens under a five-year lease, and renamed them the Churchill Park Community Gardens. Anyone can now rent a plot of land about 16 feet by 20 feet from the City for $80 a season. Raised plots are also available for gardeners in wheelchairs. The 700 birds from about 57 species, that used to be located in the Dundurn Park Aviary, can now be visited in the Gardens in a building at the end of the greenhouses.