Hylan Boulevard is a major northeast-southwest boulevard in the New York City borough of Staten Island, and the longest street in a single borough in the city. It is approximately 14 miles (23 km) long, and runs from the North Shore neighborhood of Rosebank, then along the entire East Shore, to the South Shore neighborhood of Tottenville. 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.

John Francis Hylan was the 96th Mayor of New York City, from 1918 to 1925. From rural beginnings in the Catskills, Hylan eventually obtained work in Brooklyn as a laborer on the elevated railroad. During his nine years with the company, he worked his way to engineer, and also studied to earn his high school diploma. He continued by earning a law degree. He practiced law for nine years, and also participated in local Democratic politics.