This would be my pick for the city’s funkiest green space. It's seen its share of political protests—in 1988 a standoff between the police and the homeless people living here culminated in five days of rioting and charges of police brutality—but today it’s better known for the very free expression it gives home to. The yearly dance parade ends here with a smorgasbord of dancing of all sorts (go to for more on that) and it’s here every summer that the Howl Festival ( is held. It’s a spiky mix of spoken-word performances and music, often political in nature. Best is the daily sidewalk catwalk of pierced, tattooed, fashion-forward locals. Incorporated as a park in 1878, Tompkins Square has a number of meditative green spaces, playgrounds, a swimming pool, and a smattering of undistinguished monuments. It used to have a band shell where an early version of the Grateful Dead made their East Coast debut, but that has since been torn down.