In 1857, immigrants protesting unemployment and food shortages were attacked by police. In 1863 the deadly Draft Riots occurred in the park and had an effect on Manhattan.
On January 13, 1874, the Tompkins Square Riot occurred in the park when police crushed a demonstration involving thousands of workers. The riot marked an unprecedented era of labor conflict and violence.
In 1877 5,000 people fought with the National Guard when they amassed to hear Communist revolutionary speeches.
In the middle 19th century the "Square" included a large parade ground for drilling the New York National Guard. The modern layout of the park by Robert Moses in 1936 is said to be intended to divide and manage crowds that have gathered there in protest since the 1870s. That tradition was rekindled as the park became the nursery of demonstrations against the Vietnam War in the 1960s.
By the 1980s Tompkins Square Park had become for many New Yorkers synonymous with the city's increased social problems. 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.
In August 1988, a riot erupted in the park when police attempted to clear the park of homeless people; 44 people were injured. Bystanders as well as homeless people and political activists got caught up in the police action that took place on the night of August 6 and the early morning of August 7, after a large number of police surrounded the park and charged at the hemmed-in crowd while other police ordered all pedestrians not to walk on streets neighboring the park. 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), but ultimately, although at least one case went to trial, no police officers were found culpable.
From June 3, 1991 to July 25, 1992, the park was closed to the public for restoration, but also to keep out the homeless and in attempt to calm tensions.
Increasing gentrification in the East Village during the 1990s and 2000s, as well as enforcement of a park curfew and the eviction of homeless people, have changed the character of Tompkins Square Park. The park was closed and refurbished in the early 1990s and today, with its playgrounds and basketball courts, handball courts and built-in outdoor chess tables, the park attracts young families, students and seniors as well as tourists from all over the globe. Although at the same time, the park lost much of its "culture." A New York Times reporter writes that the park is now "a lost place that has been supplanted by a neighborhood that is rather sterile and uninspiring.
There is also an annual "Riot Reunion" concert every summer called "Cracktöberfest" that features the neighborhood squatt-punk, "crack rocksteady" band Leftöver Crack or one of their many other incarnations such as Choking Victim.
The Food Not Bombs Manhattan chapter serves every Sunday in the park, rain or shine.
One such fundraiser is the Halloween party the run hosts to raise money to maintain the run. This is the biggest dog Halloween party in the United States, boasting an annual attendance of more than 400 dogs in costume and 2,000 spectators
American elm trees are known for their towering canopies, which provide abundant shade throughout the spring, summer, and fall. It is rare today to find such a collection of American elms, since many of the mature elms planted across the country have been killed by Dutch Elm Disease. This incurable disease, a fungus carried by elm bark beetles (Coleoptera scolytidae) that colonize on the branches of the elm tree, swept across the United States in the 1930s and remain a threat to the park's collection of elms. Despite having lost at least 34 of the trees, Tompkins Square Park still hosts a large assemblage of elms, which continue to this day to enchant park patrons. The East Village Parks Conservancy, a volunteer group, raises significant private funds for the ongoing care and maintenance of the American elms and other historic trees in Tompkins Square Park.
