It was renamed in 1923 for New York City mayor John F. Hylan, before which it was known as Southfield Boulevard and the northern segment as Pennsylvania Avenue.

The increased volume, built up over decades, has resulted in the road becoming New York City's newest "Boulevard of Death" according to Transportation Alternatives.

[6] It becomes divided by street markings at Tompkins Avenue, but then splits at 0.8 miles (1.3 km) and crosses the Staten Island Expressway over two separate overpasses.

[8] Half a mile later, Hylan intersects with Old Town Road and Quintard Street, at which point it begins a predominantly straight southwesterly run.

At the northernmost end is Buono Beach, a small park with views of New York Harbor, as well as the Alice Austen House (address: 2 Hylan Blvd.