The Pacific National Exhibition (PNE) has hosted a number of amusement rides since it opened in 1910; with an early roller coaster installed in 1915. However, a permanent amusement complex was not built until the 1920s. Built at Hastings Park, several rides were opened by 1926, including a Shoot the Chute ride and a new roller coaster, the Giant Dipper, to replace the one built in 1915.

Although the first rides were opened by 1926, Playland's predecessor, Happyland, did not fully open for its first regular season until 1929. Happyland was operated by several companies while it was open, including the British Columbia Amusement Company; and the Pacific Amusement Company. The park continued to operate until 1957, when amusement park operations were moved to its present location. The original site was demolished after the amusement park's relocation; with the site later being used for Pacific Coliseum.

Construction for the modern amusement park occurred from December 1957 to 1958, with the park opening in time for that year's PNE exhibition. Reopened as Playland, the park featured several new attractions including the Wooden Roller Coaster, the country's largest at the time of its opening.

Although it was located adjacent to the PNE's fairgrounds, the amusement park did not formally become a division of the Pacific National Exhibition until January 1993.

In 2001, the park begain operating Halloween-themed events or "Fright Nights" during the month of October. During this time, haunted houses are set up inside the amusement park and employed monsters are roaming the park scaring patrons. Most of the parks regular amusement rides are in operation. The haunted houses have been owned and managed by ScreamWorks Inc., a Calgary-based company. Fright Nights event and its including the haunted houses were managed by the PNE and Playland beginning in 2009.

In 2009, the Wooden Roller Coaster was designated with "classic" and "landmark" status by the American Coaster Enthusiasts.