The City bought this land for $10,000 on January 28, 1895, from Colonel John Henry Land (1846 - 1929). The original name of the site was "Land's Bush". The site was purchased and developed as a pleasure ground.
In 1897, Land's daughter, Elizabeth Reid, donated $500 for a drinking fountain to be placed on the site. The fountain was installed in 1898, in memory of her father. The area was conveyed to the Parks Board in 1912.
Woodland Park was a popular gathering place for local communists during the 1930's. On May 2, 1932, there was a Communist rally at Woodland Park. Firemen were called in to assist the police and they eventually had to turn on their hoses to disperse the crowd of over 200 people!
In 1947, grading and sowing at Woodland Park included the removal of many beautiful trees. This event had many neighbourhood residents "up in arms". However, the plans continued, with the idea that the renovations would improve the facilities for the residents in the area. In 1949, the grandstand was built seating about 1,200 spectators. In 1952, floodlights were installed for the main baseball diamond. The stand had washroom facilities for the spectators and change rooms for the players. The field house was added in 1983.
There is a plaque on the site honouring Allan Studholme (1846 - 1919). Mr. Studholme was the member for East Hamilton in the Ontario Legislature from 1906 to 1919. He was instrumental in the passing of the Workmen's Compensation Act, contributed to such reforms as the eight-hour day and minimum wage, and was a fighter in the battle for women's voting rights. He has the distinction of being the first representative of labour in the Ontario legislature, once keeping the legislature in session for 18 hours while he delivered a speech concerning the need for social legislation.