Hillcrest is an older neighborhood which has gone through gentrification, with many streets lined with trees. Hillcrest is best known for a variety of Craftsman and mid-century modern apartment buildings. The neighborhood is bound by Mission Hills to the northwest, Bankers Hill and Balboa Park to the south, University Heights to the north, and North Park to the east. A large ridge overlooking San Diego bay borders the neighborhood to the west.
Hillcrest is part of the Uptown community planning area, which consists of the neighborhoods of Mission Hills, Hillcrest, Bankers Hill, Park West, and University Heights.
Initially, Hillcrest was a chaparral-covered mesa. Kumeyaay Indians inhabited numerous villages scattered throughout the San Diego region. Spanish colonization brought the first of twenty-nine California missions with the founding of the nearby San Diego Mission. Presidio Park in Mission Hills and Old Town just down the hill are a part of San Diego history.
In 1870, Mary Kearney obtained a deed from the city for the land that eventually became Hillcrest. In 1871 Arnold and D. Choate, two real estate developers, obtained that property. George Hill, a wealthy railroad tycoon, then purchased the land. Real estate development began in 1910 and the area was built out by 1920. During the 1920s and 1930s Hillcrest was considered a suburban shopping area for downtown San Diego.
In the 1910s, Hillcrest became one of the many San Diego neighborhoods connected by streetcars and an extensive San Diego public transit system that was spurred by the Panama-California Exposition of 1915. These streetcars became a fixture of Hillcrest until their retirement in 1939.
In 1940 the “HILLCREST” lighted sign at the intersection of University and Fifth Avenue was first erected, donated by the Hillcrest Women’s Association, a group of local female shopkeepers. After falling into disrepair, it was taken down and rebuilt in 1984.
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