[4] Surrounded by a cast-iron fence the following year[5] and planted with trees, the square was expected to have a prosperous and genteel future,[6] which was undercut, however, by the Panic of 1837 that brought the city's expansion to a halt.

[8] On January 13, 1874, the Tompkins Square Riot occurred in the park when police crushed a demonstration involving thousands of workers.

[11] Organizations rejected offers of charity and instead had asked for public works programs that would provide jobs for the masses of unemployed.

The park at that time was a high-crime area that contained encampments of homeless people, and it was a center for illegal drug dealing and heroin use.

[16] Much of the violence was videotaped and clips were shown on local TV news reports (notably including one by a man who sat on his stoop across the street from the park and continued to film while a police officer beat him up),[17] but ultimately, although at least one case went to trial, no police officers were found culpable.

[17] Against that backdrop, Daniel Rakowitz shocked the neighborhood in 1989 when he murdered Monika Beerle, dismembered her, made a soup out of her body and served it to the homeless in the park.

[18] Rakowitz, called the Butcher of Tompkins Square, was found not guilty by reason of insanity and remains incarcerated at the Kirby Forensic Psychiatric Center on Wards Island.

[25] Since the 1980s, the asphalt that covers the multi-purpose courts at Tompkins Square Park has served as a skatepark and training grounds for multiple generations of skateboarders.

[38] Since the 1980s, the asphalt that covers the multi-purpose courts at Tompkins Square Park has served as a skatepark and training grounds for generations of skateboarders.

[41][42] Many acclaimed skateboarders, including Tyshawn Jones, Alex Olson, Yaje Popson, Jarrod Brandreth, Harold Hunter, Ted Barrow, Andy Kessler, Zered Bassett, Jake Johnson, and others, have skated Tompkins Square Park, using it as a training facility.

[42] Skateboarders have protested this plan, with TF local Adam Zhu starting an online petition that garnered over 30,000 signatures.

[45] Zhu worked with Steve Rodriguez, Carlina Rivera, Mitchell Silver, Supreme, and others to bring awareness to the turfing controversy.

[46] On Friday September 6, 2019, one day before the rally was set to take place, the Parks Department announced that they intend to keep the asphalt, scrapping plans to put down synthetic turf.

It now includes a surface of crushed stone [sand], three swimming pools, a tree deck, and bath areas and hoses to spray off one's pet.

[51] For 32 years, the run hosted the annual Tompkins Square Halloween Dog Parade to raise money for its own maintenance.

Indian Sadhu A.C. Bhaktivedanta Swami Prabhupada came to sing and preach at the park in 1966, beginning the worldwide Hare Krishna movement.

This neo-classical fountain was a gift of the wealthy San Francisco dentist, businessman, and temperance crusader Henry D. Cogswell (1820–1900).

The fountain is a square granite kiosk with four stone columns supporting a canopy on whose sides the words "Faith," "Hope," "Charity," and "Temperance" are chiseled.