Madison Square, now found at the fabled intersection of 23rd Street and Fifth Avenue, dominated by the brilliant triangle of the Flatiron Building, used to be a swamp. Then it was a Potter’s Field, an arsenal, and the location of a farmhouse-turned-roadhouse named Madison Cottage. Back in the early 1880s, this part of Manhattan marked the civilization of downtown from the farmland and forests above. By 1847, however, as newcomers to the city pushed the boundaries ever northward, the area became a designated park, presided over by the sumptuous Fifth Avenue Hotel.
By the 1870s, so many of the city’s elite had moved uptown that the Madison Square area was more commercialized, chockfull of hotels and clubs and restaurants. Eventually, the Madison Square Garden hall, designed by Stanford White, was built. White was a brilliant architect but also a naughty old goat who designed a love-nest for himself in the building. He had fallen madly in love and seduced the young (16 years old!) and beauteous actress Evelyn Nesbit, the wife of one Harry K. Thaw who was as mad as he was rich. Up on the rooftop restaurant of Madison Square Garden, on the night of June 25, 1906, Thaw walked up to White and shot him in the head. It was a huge scandal, and the basis for the book and musical, Ragtime.
Like so many other city parks, as the 20th century progressed, Madison Square became woebegone and neglected, especially as White’s Garden was torn down and replaced by a nondescript monstrosity that still stands above Penn Station at 32nd Street and Seventh Avenue. It was haunted by junkies at night, in the 1970s and early 1980s, but a city revitalization program cleaned it up and brought it back to life. When the Shake Shack (home of great burgers, milkshakes, and ridiculously long lines) enticed the masses in the summer of 2004, and a wonderful kids’ playground at the northeast end opened around the same time, Madison Square Park became a destination for families again.
The free music here is worth investigating before you go, as well as the art exhibitions and talks. Not everything in New York has to be ticketed and expensive.
I suggest you head over to Little India beforehand—a short walk away on Lexington Avenue around 28th St—and big up some yummy curry for your picnic. What could be better than a warm day, a roti and a mango lassi, good company, and a lovely playground for the kids to run around in while you relax and listen to a band, or wander and look at the art exhibitions.