The land that would become Owl's Head Park was first settled by the Canarsee.^[1] In the 17th century, Dutch settlers arrived in the area.^[1] The first European to claim ownership of the park's land was Teunis Van Pelt.^[2] On April 13, 1680, he sold a section of his land to Swaen Janse Van Lowaanen, whose farm on the water, north of what is now known as Bay Ridge Avenue, eventually became the park.^[2] The land passed through several more hands before ending up with Henry C. Murphy, who in 1856 built a large mansion on the property, creating a personal estate.^[2][3] Murphy was a state senator best known for writing the legislation that began construction on the Brooklyn Bridge. The famous bill was signed in his mansion at Owl's Head, which was a name he bestowed on the property.^[2][3] The source of the name has been a subject of debate, ranging from the shape of the land, to speculation that owls once lived in a barn on the property, to the fact that stone owls once graced its entrance gate.^[2][3][1] It seems likely, however, that the name was simply lifted from another property in the area, that of the Van Brunt family, whose land really was shaped like an owl.^[2][4][5]

Murphy sold the property to Eliphalet Williams Bliss, founder of the E.W. Bliss Company.^[2] The park is known to some as "Bliss Park" for this reason. Bliss expanded the property by buying nearby land and added new structures to the estate.^[2][3] These structures included a long driveway, a keeper's lodge, a stable, and an observatory and tower.^[3][2] As early as 1894, Bliss embraced the idea of his property one day becoming a public park.^[3] After his death in 1903, his will stipulated that the property be sold to the city for a reduced price, but only if it was to be used as parkland.^[1] For various reasons, the city did not buy the property until 1928.^[2] These delays caused parts of the property to be lost to other purchasers, including the portion directly along the water, which has been home to a wastewater treatment plant since 1952.^[2] Financial limitations and lack of political will also led to the demolition of the property's mansion and observatory tower in 1932.^[2] By 1940, the stables were also demolished.^[2]

In the following decades, improvements to the park were made by the Parks Department under Robert Moses, including paths, playing fields, benches and restrooms.^[2] In the 1960s and 70s, however, the park suffered from decline during the city's fiscal crisis.^[2] In the 1990s, Brooklyn's borough president and the city council dedicated significant funds to revamp the park.^[2] The original wrought iron gates from Bliss's estate, with his initials on them, were reinstalled at the park's southeastern entrance in 2004.^[1]

Owl's Head Park is located on a glacial moraine and thus has rich soil to support its many trees, including pines, locusts, oaks, maples, corks, beeches, and a tulip poplar.^[1] The park's land slopes upward towards the water, providing views across New York harbor to Manhattan, Staten Island, and New Jersey.^[1] The sloping terrain of the park also makes it a popular place for sledding in the winter.^[6][2] The park has basketball courts, a playground, spray pool, and dog run, as well as a well-known skate park.^[6] The park's basketball courts are named for William D. "Billy" Lake, a local firefighter who lost his life on September 11, 2001.^[7] The courts were named in honor of Lake in 2004.^[7]

The park often hosts local events, such as Viking Fest, which honors the area's history of Scandinavian immigration,^[8] Halloween events,^[9] and the city's annual Mulchfest event for Christmas tree disposal.^[10] In 2022, Owl's Head Park was the site of the first-ever Gay Ridge Pride, an LGBTQ pride event for all of Southern Brooklyn and the neighborhood's first pride celebration.^[11]