Highland Park—the 2.2 square-mile residential “island city” four miles north of downtown Dallas—brims with opulence. Boxwood hedges, freshly mowed lawns, and ivy-festooned homes line the pristine streets. Hermes purses swing to-and-fro on the shoulders of Highland Park Village shoppers while natty golfers spot the Dallas Country Club course with divots. So why, exactly, does this little city exist in the middle of the second-largest city in the state?

A reasonable question, though you might be clamoring for a bit of history before I give an answer. The Philadelphia Place Land Association purchased what is now Highland Park in 1889 for an average price of $377 an acre—the total came to $500,000. The association planned to fill the land with homes modeled after parkland housing in Philadelphia. The panic of 1893 that subsequently brought an end to the Dallas land boom eventuated in the end to this development as well—Henry Exall, the acting agent of the land association, watched his own fortune vanish and opted to build a horse breeding farm on the land rather than continue a development he could no longer afford. In 1906 Exall sold the land to John Armstrong.

Armstrong had similar aspirations for the area (minus the Philadelphian touches). The land rests sufficiently above downtown Dallas to afford a pleasant view, so the new proprietor appropriately named the land Highland Park. With Wilbur David Cook (a Beverly Hills landscape architect) and George E. Kessler (the designer of Fair Park), Armstrong began development—the men allotted 20 percent of the original land to park use and started construction on the remaining acreage. Armstrong, Cook, and Kessler persuaded buyers to purchase land with clever phrases describing the area: “Beyond the City’s Dust and Smoke” and “It’s Ten Degrees Cooler in Highland Park.”

In 1913 Highland Park asked Dallas to annex the area. Dallas refused, so the residents chose to incorporate—Highland Park became a city (population 1,100) in 1915. The city continued to expand as addition after addition piled onto the land, and Dallas came to regret its unpropitious decision. Roles shifted (let’s say 180 degrees) when a repenting Big D filed for annexation. Highland Park residents balked at the idea and fought Dallas until 1945, the year of the final failed annexation attempt. Growth marked the years preceding 1945—the population rose to 8,422 and 1931 marked the opening of the Mediterranean-styled Highland Park Village (commissioned by Armstrong’s sons-in-law Hugh Prather and Edgar Flippin, it was the first large-scale shopping center in the United States). Dallas retaliated as any other sizable city would; it surrounded Highland Park and choked its hopes for expansion.

The strictures on growth stinted population increases (approximately 8,900 now live in the city), but marks of distinction continued to arrive. The U.S. Department of the Interior named Highland Park Village a National Historic Landmark (the arrival of stores such as Chanel, Christian Dior, Polo/Ralph Lauren, and Escada probably have provided residents with a more tangible thrill), and Newsweek magazine included Highland Park High School in its 2003 list of top high schools in the country. So the Highland Park moniker still rings true—with such accolades, how can residents deny that they truly have a view from the top?