This is a self-guided tour that covers three separate New York City neighborhoods: Gramercy Park, Union Square and Stuyvesant Square, all are historic districts. This tour should take you between 90 minutes and 2 hours to complete. You may want to consider combining this with our self-guided Flatiron District tour or any of our self-guided New York City Tours. Oh yes, we also offer guided tours.
There are many subway and bus lines that service this tour of Gramercy Park and Union Square. To reach the start of our tour, it's best to use this link for directions from anywhere in the NYC area. Be sure to read our posts on navigating the New York City subway and getting help with buying a MetroCard.
If you are considering using one of the hop-on, hop-off double decker buses to make your way through NYC, please note that several have bus stops that are very close to locations on this tour. Please read our post comparing the different New York City bus tour options.
GRAMERCY PARK HISTORIC DISTRICT East 18th-21st Streets between Park Avenue South and 3rd Avenue
Many well-known figures have lived in this historical and lovely residential district from actors, artists, authors, politicians and members of New York’s high society. If you want a peaceful stroll that will bring you back to another era in New York’s past, Gramercy Park is a great destination.
A - Gramercy Park East 20th-21st Street between Gramercy Park West and Gramercy Park East
This is Manhattan's only private park and only residents of the 39 buildings surrounding the park are given keys to unlock the gates. Besides being a serene oasis for the lucky key-holders, the park and its environs are quite historic. The townhouses that border the park are some of the oldest in the city and among the former residents are renowned architect Stanford White and author Oscar Wilde. Two presidents, Teddy Roosevelt and John F. Kennedy, played in the park when they were children.
B - Gramercy Park Hotel corner of Gramercy Park North and Lexington Avenue
This boutique hotel opened in 1925. Many notable guests have stayed at the hotel including the Joseph P. Kennedy family, including a young John F. Kennedy. Humphrey Bogart married his first wife at the hotel and Babe Ruth was a regular bar patron. Because the hotel is top-notch for service as well as discreet, they have attracted many celebrities over the years including Bob Dylan, Madonna, and David Bowie. Today, the hotel has a bohemian-chic style and exhibits paintings by noted artists, including Jean-Michel Basquiat, Damien Hirst, Julian Schnabel, Cy Twombly and Andy Warhol.
Famous Gramercy Park residents
Actor James Cagney once lived at 34 Gramercy Park East as did Margaret Hamilton who played the green-tinted Wicked Witch of the West from The Wizard of Oz. Down the street at 36 Gramercy Park East actor John Barrymore lived at from 1910-1916. On the bnorth of the park, at 38 Gramercy Park North, John Steinbeck, author of The Grapes of Wrath and other great American novels, lived here in 1925 for a few months at the start of
his career in a small room on the 6th floor. Thomas Edison lived for some time at 24 Gramercy Park South near the Manhattan studio of the Edison Manufacturing Company on East 21st Street. After he moved in 1908, the original house was torn down and the current one was erected.
C - The Players Club 16 Gramercy Park South
This social club was founded in 1888 by actor Edwin Booth. You may recognize the last name. It was Edwin’s brother John Wilkes Booth who assassinated President Lincoln in 1865. The Players Club, which remained a “men only’ club until 1989, has an impressive list of past and present members such as Mark Twain, actors James Cagney, Sidney Poitier and Kevin Spacey, playwright Eugene O'Neill, journalist Walter Cronkite, musical performers Liza Minnelli and Tony Bennett. Even late night talk show host Jimmy Fallon is a Player. Unfortunately, the Players Club is not open to the public but The Hampden-Booth Theatre Library is open by appointment only. The library is a unique collection of rare 19th century American and British Theatre memorabilia, books, photos, prompt-books, stage costumes and props. Click here for more information on how to schedule a visit to the library.
In the early 1900s, American art was beginning to gain attention, whereas previously, the focus of art lovers had been European art. In 1898, Charles De Kay, the literary and art critic for The New York Times, collaborated with a group of distinguished artists and wealthy art patrons to open a gathering place for American artists and art lovers. The club is housed in a historic mansion once owned by Samuel Tilden, the 25th Governor of New York State. The National Arts Club hosts both members-only and public events and their four galleries are open to the public for free from Monday-Friday 10 am-5 pm.
E - Theodore Roosevelt Birthplace National Historic Site 28 East 20th Street
America's 26th President was born here on October 27, 1858, and lived here until he was 14 years old. The original building was demolished in 1916, but a reconstruction was built in 1919 and the interior is filled with many of the original furniture and objects from Roosevelt’s first home. You can also see some of his taxidermy specimens collected from his famous hunting outings. Prior to becoming president, Roosevelt devoted much of his career to New York, serving as a New York State assemblyman then becoming the president of the Board of Police Commissioners and eventually the 33rd Governor of New York State. Note: Closed as of July 1, 2022 until further notice.
This tavern pulled its first pint of their home-brewed ale in 1864. They have been operating as a bar and restaurant continuously since then (secretly serving alcohol during Prohibition) and it is one of the oldest taverns in the city. The décor, such as the intricately carved wooden ba,r will take you back in time to the 1860's. Because it is frequented by locals, it’s been used as the set in New York TV shows like Seinfeld (episode “The Sniffing Accountant”) and Sex in the City. If you are a SATC fan, we have a self-guided Sex and the City tour. And you should definitely take a look at our post Where is Carrie Bradshaw's apartment located?
G - O. Henry’s House 55 Irving Place
Prolific author O. Henry (born William Sydney Porter) lived here when he wrote his best-known story The Gift of the Magi. During his time on Irving Place from 1903-1907, O. Henry visited Pete’s Tavern often. He died in 1910 from cirrhosis of the liver caused by excessive drinking. He was only 47 years old.
H - Washington Irving’s House 120 East 17th Street
Despite the plaque on the 17th Street facade, there is no evidence that the author of The Legend of Sleepy Hollow and Rip Van Winkle ever lived here. It is true that Irving Place was named in honor of Washington Irving as the developer of Gramercy Park, Samuel Ruggles, named the small street south of the park for Irving. It is also true that Washington Irving’s nephew, Edgar Irving, did live in the building next door and he named his son Washington, after his uncle. Still, it is a lovely building.
UNION SQUARE DISTRICT East 14th to East 17th Streets between 4th Avenue and Broadway
For over 150 years the area has been a hub of shopping, commerce, entertainment and political activism. Union Square has a frenetic energy similar to the pace of Midtown but with the hip feel of downtown. In the early 1800s the area was rural with a potter’s field (cemetery for the poor). In 1807, two major roads intersected here and this intersection was designated as Union Place because of the ‘union’ of these two roads, Bloomingdale Road (now Broadway) and Bowery Road (now 4th Avenue). By the 1850s, the area surrounding Union Place was filled with elegant mansions, hotels, stores, and banks.
Surrounded by modern buildings, this stately white granite bank was built in 1906 and designed by Henry Bacon. The building’s Corinthian Temple design was a sign of bigger and better things to come from Bacon. He went on to design the Lincoln Memorial in Washington, DC. Since 1996, the Union Square Savings Bank Building has been owned by producer Daryl Roth and houses the Daryl Roth Theatre dedicated to unique theatrical productions such as the current sensation, Fuerza Bruta.
J - Union Square Park
The park is fantastic for people-watching, a New York pastime. It’s always filled with locals hanging out, workers eating lunch, skateboarders, musicians, and families playing in the playground. If you are a dog-lover, there’s a dog run on the west side of the park and is especially fun to watch. In the early 1800s, the park was smaller and named Union Park, but was renamed, and it was expanded in 1871 and redesigned by landscape architects Frederick Law Olmsted and Calvert Vaux (of Central Park and Prospect Park fame). Inside the park are statues in honor of political world figures: a bronze George Washington mounted on a horse (1856), Marquis de Lafayette (1876) and Abraham Lincoln (1870). Just outside of the southwest corner of the park, on a traffic island, is Mohandas Gandhi (1986) who looks out of place standing on a traffic island with cars and taxis rushing by.
This world-famous outdoor year-round market was created in 1976 to give local farmers to sell their fresh produce to city dwellers seeking just-picked fresh fruits and vegetables, award-winning cheeses, artisan breads, jams, pickles, an abundance of cut flowers and plants, wine, ciders, maple syrup and so much more. The market is open on 8am-6pm on Mondays, Wednesdays, Fridays and Saturdays.
L - Ladies' Mile Historic District 15th to 24th streets between Park Avenue South to 6th Avenue
From 1865 to 1914, these streets were lined with the original store locations of many of the most famous and fashionable department stores of the day, including Lord & Taylor and Bergdorf Goodman (both now located on 5th Avenue). Tiffany & Co. had its store on the corner of Union Square West and 15th Street from 1860-1906, when they also moved to 5th Avenue. Ladies’ Mile includes the Flatiron Building, visited in our self-guided Flatiron Tour.
Speaking of shopping, go into the Burlington Coat Factory on the south side of the park. Their plate glass windows on the top floors offer a great view of the park and the lovely, landmark buildings that surround it.
Tip: The subway station at Union Square is great place to see some of the best subway musicians and buskers. Our post about Where to find New York City Street Performers and Subway Music will lead you to right to them!
STUYVESANT SQUARE HISTORIC DISTRICT 14th to 18th Streets from 1st to 3rd Avenue.
M - Stuyvesant Square Park 15th-17th Streets between Rutherford and Nathan D. Perlman Place
Two blocks east of Irving Place is a four acre park surrounded by the oldest cast-iron fence in New York City. Thankfully, you don’t need a key enjoy the serenity of the fountains, lawns and flower beds. For botanists, you can see specimens of original trees planted in the park including Old English Elms and Little Leaf Lindens. The park is named for Peter Gerard Stuyvesant, an ancestor of Peter Stuyvesant, the last Dutch governor of New Amsterdam before it became British New York. In 1836, the wealthy Stuyvesant and his wife sold the land to the city for only five dollars for the sole purpose of being turned into a public park. The streets surrounding the park developed into a desirable, elegant residential area. Today, the park is enjoyed by locals, students from the nearby Friend’s Seminary and employees of the massive Beth Israel Medical Center located across the street.
N - St. George's Episcopal Church 209 East 16th Street across from Stuyvesant Square
This New York City and National Historic Landmark was built in 1856 and is considered to be one of finest examples of the Early Romanesque Revival architecture movement in America. The original St. George's was built in 1752 by Trinity Church near in Lower Manhattan and in 1856 they built a new church on what was then a very fashionable Stuyvesant Square. For many years millionaire J.P. Morgan the church's most influential parishioner and the St, George’s was referred to informally as "Morgan's Church".
O - Friend’s Seminary 222 East 16th Street
Right next to Stuyvesant Square is this prestigious private school established by members of the Religious Society of Friends, known more commonly as Quakers. The seminary was founded just after the end of the American Revolution as the Friends' Institute and was located on Pearl Street in Lower Manhattan. At that time, New York City had hardly developed beyond Chambers Street. But as Manhattan grew northward the Institute moved and landed in its current location in 1860 and changed its name to Friends’ Seminary. In 1915, tuition was $250 a year. Today it’s $37,000 a year!