Highland Park, on State Highway 289 and State Highway 75 four miles north of downtown Dallas in central Dallas County, is a 2.2-square-mile residential "island city" surrounded by Dallas on the south, east, and west and University Park on the north. In 1889 the land was bought by a group of Philadelphia investors, the Philadelphia Place Land Association, for an average price of $377 an acre, or $500,000 total. Henry Exall, acting as agent, intended to develop the land along Turtle Creek as Philadelphia Place, an area of exclusive housing modeled after parkland housing in Philadelphia. He laid out gravel roads and built a dam across Turtle Creek to form Exall Lake before the panic of 1893 destroyed the Dallas land boom and ended the development. Exall lost everything except his horse and some of the land. He subsequently began a breeding farm, Lomo Alto Horse Farm. During the 1890s Exall Lake was a favorite picnic destination for Dallasites. Bass and perch abounded in it, and a steamboat operated on it. Exall bred horses with his stallion Electrite until 1906, when John Armstrong bought the land for a residential development.
Armstrong had been a partner of Thomas L. Marsalis in the development of Oak Cliff but sold out to open a meatpacking business. With the sale of his business he invested the money in 1,326 acres of the former Philadelphia Place land to develop under the name Highland Park. Armstrong, along with his sons-in-law Hugh Prather and Edgar Flippen, gave Highland Park its name because of its location on high land overlooking downtown Dallas. The investors hired Wilbur David Cook, a landscape architect of Beverly Hills, California, to design the layout. In addition, George E. Kessler, who designed Fair Park and much of downtown Dallas, was hired to help in planning and development. Twenty percent of the original land was set aside for parks. The first 100-acre addition was begun in 1907 and promoted with the slogan "Beyond the City's Dust and Smoke." Later appeared the slogan "It's Ten Degrees Cooler in Highland Park." The second development in Highland Park, the Lakeside addition, was developed in 1910.
In 1913 Highland Park asked Dallas for annexation but was refused. The 500 residents therefore voted to incorporate, on November 29, 1913. The incorporation officially took place in 1915, when the population was 1,100; W. A. Fraser was the first mayor. Highland Park set up its own waterworks, which it operated until 1932. In 1915 the third addition to Highland Park was built, and two years later a fourth. After two years a long annexation controversy began. The city of Dallas regretted its earlier refusal to annex Highland Park and began a battle that lasted until 1945, when Dallas was turned down for the last time. The last major land development in Highland Park, Highland Park West, was built in 1924. In 1931 Highland Park Village, the first shopping center of its type in the United States, was constructed in Highland Park.
By 1933 Highland Park had a population of 8,422 and twelve businesses. Its resident population was large, but few businesses and no industry operated in the city. From 1932 to 1950 Highland Park bought water from the city of Dallas, but in 1950 Highland Park and University Park, the "Park Cities," began their own waterworks. In 1949 Highland Park had four elementary schools, a junior high, and a high school. Later the Park Cities combined their school districts, as they did their newspapers. The Park Cities News was established in 1938 and the Park Cities People in 1981. In the late 1950s Highland Park had a population high of 12,900, before beginning its slow decline to its 2010 level of 8,564. After its attempt to annex Highland Park was defeated, Dallas annexed the land around it. Highland Park was forced to grow only by building houses on the few remaining vacant lots, or by tearing down old buildings to construct new ones. As a result, the community became known for its strict zoning ordinances. Its reputation for quality housing was enhanced by the abundance of parks running along Turtle Creek and by the Dallas Country Club, which is in Highland Park. In the 2013–14 school year the Highland Park Independent School District had four elementary schools, one intermediate school, one middle school, and one high school serving approximately 7,000 students from Highland Park, University Park, and portions of North Dallas.