In the 1910s, Hillcrest became one of the many San Diego neighborhoods connected by the Class 1 streetcars and an extensive San Diego public transit system that was spurred by the Panama-California Exposition of 1915 and built by John D. During the 1920s and 1930s Hillcrest was considered a suburban shopping area for downtown San Diego. Real estate development began in 1910 and the area was built out by 1920. George Hill, a wealthy railroad tycoon, then purchased the land. Choate, two real estate developers, obtained that property. In 1870, Mary Kearney obtained a deed from the city for the land that eventually became Hillcrest. Presidio Park in Mission Hills and Old Town just down the hill are a part of San Diego history. Spanish colonization brought the first of twenty-nine California missions with the founding of the nearby San Diego Mission. Kumeyaay Indians inhabited numerous villages scattered throughout the San Diego region.

Initially, Hillcrest was a chaparral-covered mesa. ( November 2011) ( Learn how and when to remove this template message)

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