Broadway forms a dividing line between Chelsea to the west and the area that comprises Union Square and Gramercy Park . It is here, between the great avenues - Third, Park and Fifth - that midtown Manhattan's skyscrapers begin to rise from the low-lying buildings. Before heading on to those jaw-droppers, like the Empire State Building, it's certainly worth at least a jaunt around the more genteel parts of these two neighborhoods, which offer some decent architecture themselves, like the Flatiron Building . The #N, #R, #Q, #L, #W, #4, #5 and #6 trains all stop at Union Square.

Explore Union Square and Gramercy Park

Gramercy Park, Irving Place and around,  Madison Square and the Flatiron Building,  North of Madison Square, Union Square

Gramercy Park
Manhattan's clutter suddenly breaks into the ordered open space of Gramercy Park , a former swamp between 21st and 22nd streets that divides Irving Place and Lexington Avenue. It is one of the city's prettiest squares. Its center is beautifully planted and completely empty for much of the day, for it is the city's last private park and the only people who can gain access are those rich or fortunate enough to live here. Famous past key holders have included Mark Twain and Julia Roberts, never mind all those Kennedys and Roosevelts.

Have a walk around the square to get a look at the many early-nineteenth century townhouses. The Players at 16 Gramercy Park S was created in 1888 when actor Edwin Booth turned his home into a private club for play and socializing, at a time when theater types were not accepted into regular society. Members have included Irving Berlin, Frank Sinatra and Winston Churchill - women were not admitted until 1989.

Next door, at no. 17, the School of Visual Arts occupies the former home of Joseph Pulitzer, while at the northeastern corner of the square, no. 38, is the mock Tudor building in which John Steinbeck, then a struggling reporter, lived between 1925 and 1926. At 52 Gramercy Park N stands the imposing 1920s bulk of the old-fashioned Gramercy Park Hotel , whose early elite residents included Mary McCarthy, a very young John F. Kennedy and Humphrey Bogart with first wife, Mayo Methot. Lining Gramercy Park West is a splendid row of brick Greek Revival townhouses from the 1840s.

Irving Place and around
Manhattan's clutter suddenly breaks into the ordered open space of Gramercy Park , a former swamp between 21st and 22nd streets that divides Irving Place and Lexington Avenue. It is one of the city's prettiest squares. Its center is beautifully planted and completely empty for much of the day, for it is the city's last private park and the only people who can gain access are those rich or fortunate enough to live here. Famous past key holders have included Mark Twain and Julia Roberts, never mind all those Kennedys and Roosevelts.

Have a walk around the square to get a look at the many early-nineteenth century townhouses. The Players at 16 Gramercy Park S was created in 1888 when actor Edwin Booth turned his home into a private club for play and socializing, at a time when theater types were not accepted into regular society. Members have included Irving Berlin, Frank Sinatra and Winston Churchill - women were not admitted until 1989.

Next door, at no. 17, the School of Visual Arts occupies the former home of Joseph Pulitzer, while at the northeastern corner of the square, no. 38, is the mock Tudor building in which John Steinbeck, then a struggling reporter, lived between 1925 and 1926. At 52 Gramercy Park N stands the imposing 1920s bulk of the old-fashioned Gramercy Park Hotel , whose early elite residents included Mary McCarthy, a very young John F. Kennedy and Humphrey Bogart with first wife, Mayo Methot. Lining Gramercy Park West is a splendid row of brick Greek Revival townhouses from the 1840s.

Madison Square and the Flatiron Building

#N or #R to 23rd Street.

Northwest of Gramercy Park, where Broadway and Fifth Avenue meet, lies Madison Square . Though a maelstrom of cars and cabs, buses and dodging pedestrians all around, the grandiose architectural quality of the surrounding buildings and the newly renovated park-space in the square's center lend it a neat seclusion that Union Square has long since lost. Rumor has it that baseball as we know it was invented here in 1845, when the Knickerbocker Base Ball Club played the first game to adhere to Alexander Cartwright's rules.

The lofty, elegant yet decidedly anorexic Flatiron Building (originally the Fuller Construction Company, later renamed in honor of its distinctive shape), set on a triangular plot of land on the square's southern side, is one of the city's most well-known buildings. It's now hard to believe that this was the city's first true skyscraper, hung on a steel frame in 1902, its full twenty stories dwarfing all the other structures around.

North of Madison Square
Lexington Avenue begins its long journey north at Gramercy Park: if you're heading uptown on the East Side from here, you'll pass the lumbering 69th Regiment Armory at 25th Street, the site of the celebrated Armory Show of 1913, which brought modern art to New York. It is now a venue for antiques shows and art fairs. Between 27th and 30th streets, one of Manhattan's most condensed ethnic enclaves, Little India , aligns Lexington. Blink, and you might miss this altogether: most of New York's 180,000 Indians live in Queens, yet there's still a sizeable handful of restaurants and fast-food places - slightly outnumbered by those down on E 6th Street - and a pocket of spice shops and fabric stores.

Union Square
Once the elegant center of the city's theatrical and shopping scene, Union Square , where Broadway, Fourth and Park avenues meet between 14th and 18th streets, invites you to stroll its paths, feed the squirrels and gaze at its array of statuary. Unfortunately, the proliferation of chain cafés and superstores around make it impossible to forget you are on the fringes of the most commercial part of New York, but the park is still a welcome respite from the crazed taxi drivers and rushed pedestrians just south. Following September 11, 2001, Union Square was the scene of candlelight vigils attended by thousands.

Explore Union Square 

Farmer’s Market
On Mondays, Wednesdays, Fridays and Saturdays  from 7am until 6pm, Union Square plays host to the city's best and most popular greenmarket on its northern edge. Farmers and other food producers from upstate New York, Long Island, New Jersey and as far as Pennsylvania Dutch country sell fresh fruit and vegetables, baked goods, cheeses, eggs, meats, fish, plants and flowers. The quality of the produce is generally very high and buying picnic fodder from the market to concoct a feast is one of the finest things you can do here on a spring or summer's day