Westmoreland Park began as a part of a residential subdivision that was subtracted from the Ladd Estate's Crystal Spring Stock Farm in 1909. By the 1930s, the site east of the subdivision had been converted from a wetland to serve time as a dairy, brickyard, and airstrip known as Broomfield Field (named after a Reed College Graduate by the name of Hugh Broomfield who lost his life over German Lines in WWI while on a recon mission.) However, as development increased, residents requested that these empty fields be turned into a city park.
In 1935, the City Planning Commission recommended development of recreational amenities for the nearby residents and "the improved appearance and traffic safety of McLoughlin Boulevard as a major traffic freeway entrance to the city." In January 1936, the City of Portland purchased the 45-acre parcel called Fairways Addition from Oregon Iron & Steel Co., a business owned by the Ladd Estate Co.
The Commission proposed a plan, prepared by architect Francis B. Jacobberger, for the park. The City of Portland and the Federal government began to develop the vision of Jacobberger’s plan as a ‘make work’ proposal under the Works Progress Administration (WPA). The WPA projects resulted in a casting pond, a model yacht lagoon (known as the Duck Pond), a fly caster’s club house, bridges, a water supply for the casting pond supplied from Eastmoreland Golf Course, and grading of the athletic fields. In August 1936, the hand-excavated, 410' x 350' casting pond served as the site for the 28th International Casting competition. Other amenities in the Jacoberger Plan included archery and croquet fields; badminton, volleyball, tennis, handball, and basketball courts; horseshoe pits; night illumination of the casting pond; and dressing room buildings. However, additional park projects remained idle for several years due to lack of funding.
In 1938, Nick Sckavone, a southeast Portland druggist who devoted a good part of his life to the development of both amateur and professional baseball in the city, began a successful campaign to advocate for a ballfield for adult baseball. In 1939, $197,299 was allocated by the City; $42,000 was used to build the baseball field. The very first baseball season got underway in 1940 and since that time, Westmoreland Baseball Park has been the launching ground for several professional careers and championship teams. In 1942, the City added a wooden stadium. The field needed lights, but city funds were not available. Not deterred, Sckavone and the Portland Amatuer Baseball Association (PABA), which he founded, organized a benefit baseball game at the old Vaughn Street Park, after which Sckavone handed the City a check for $2,000. Impressed by this show of support, the City budgeted the additional $11,000 and new lights were installed in 1945. In 1955, the facility was renamed Sckavone Field in honor of the man who was so instrumental in its creation. When Portland's citizens passed the Parks Improvement Levy in 1989, $375,000 was earmarked to rebuild Sckavone Stadium. The new structure was dedicated June 23, 1992.
In 1945, lawn bowling facilities were constructed; the grass playing surface is also used croquet and the gravel playing surface is used for petanque. A restroom/picnic shelter, originally called the Field House, was built in 1949, and a children’s wading pool in 1952. Installed in 1979, Uroboros, the name for an ancient Egyptian and Greek symbol that depicts a snake that bites its own tail, was created by Charles Kibby.
During the 1940s the first incidents of Crystal Springs overflowing its banks were documented. In 1974 it was reported that the concrete walls which channelized Crystal Springs Creek were failing. Also, in the 1970s, complaints were registered about ducks and geese creating menacing situations, dogs running loose, and parking problems. During the 1980s, swimming in the casting pond and Crystal Springs became a concern for local residents and PP&R staff because of water quality and safety issues. From 1996 to 1998, periodic flooding in the park inundated picnic areas, playgrounds, and paths. When the waters finally receded, leaving behind damaged stream edges and dying trees, questions about the future of the creek and park arose.
In order to address these issues, a master planning process for the park, with community input, began in 2002; a final plan was approved in 2003.