Stretching from East 59th Street all the way up to 110th Street, from Fifth Avenue eastward to the river, the elite Upper East Side has since the 1800s been the place to live for Manhattanites who value the cachet of their address; the latest United States Census claims that the Upper East Side had the highest per capita income of any urban quarter in the nation.  

The 50+ blocks of the Upper East Side are home to some of Manhattan’s most luxurious residences. During America’s Gilded Age, Fifth Avenue was known as “Millionaire’s Mile.” Generations later, with many of the most fantastical spaces converted to alternate use, it is referred to as “Museum Mile.”

Our walking tour will start at the foot of the Upper East Side on 59th Street and Central Park. Begin by marching north on Fifth Avenue with the park on your left and sumptuous architecture on your right...

1. 
Sherry-Netherland Hotel
781 Fifth Avenue, northeast corner of 59th Street

Architects Leonard Schultze and S. Fullerton Weaver teamed up in 1921 and set about building some of the Roaring Twenties’ grandest hotels. This French Renaissance-inspired, 38-story hotel/ apartment from 1927, topped with fanciful chimneys and stuffed with gargoyles and griffins, was one of their best. Although it was the tallest residential building in New York City there were only 165 apartments and 54 hotel rooms, allowing plenty of room for the well-heeled clientele to spread out.

2.

Metropolitan Club
1 East 60th Street, northeast corner of Fifth Avenue

The Metropolitan Club organized in 1891 as a private gentleman’s club. The membership roster was studded with Vanderbilts and Roosevelts and financier J.P. Morgan was the first president. Club member and celebrated architect Stanford White, working with a $1.6 million budget, executed thestately clubhouse in the image of an Italian palazzo with brick exterior walls covered in limestone and elegant interiors gilded and slathered in marble.

3. 
Pierre Hotel
795 Fifth Avenue, southeast corner of 61st Street

Charles Pierre Casalasco was born into the hospitality industry. His father, Jacques Pierre, was owner of the fashionable Hotel Anglais in Monte Carlo, where Charles worked as a pageboy. He sailed to New York when he was 25-years old and after a decade was able to open Pierre’s on the Park at 230 Park Avenue that became one of the city’s hottest eateries of the Roaring 20s. Casalasco sold out and began construction of Pierre’s, a $15,000,000, 714-room hotel tall enough to command unobstructed views of Central Park. Architects Leonard Schultze and S. Fullerton Weaver provided a Georgian structure of granite and cream-colored brick and topped it with a tall tower of gleaming copper, inspired by a French chateau. The Pierre opened to great fanfare and was quickly the toast of the town. Almost as quickly it was also in bankruptcy, a victim of the Depression. The Pierre was sold at a public auction on January 12, 1933 and Charles Pierre Casalasco died the following year. In 1938, oil tycoon John Paul Getty purchased the hotel for $2.5 million and the Pierre was once again on the upswing. In 1950, it became the first hotel to install radio and television sets in all the guest rooms. In 1959, The Pierre became a cooperative, and 75 apartments were sold to individual private residents, including Elizabeth Taylor. The remaining guest rooms, restaurants, bars and reception rooms continued to be patronized by a devoted international clientele. 

TURN RIGHT ON EAST 64TH STREET. 

4. 
Knickerbocker Club
2 East 62nd Street at Fifth Avenue

Along with the Metropolitan Club and the Union Club, the Knickerbocker is considered one of the bastions of old-world society. Known informally as “The Knick,” the club was founded on the evening of October 31, 1871 by 18 members of the Union Club. Early meetings were held at Delmonico’s until the first clubhouse opened on February 2, 1872, a few blocks from Delmonico’s and Union Square. The present clubhouse by William Adams Delano of the architectural firm of Delano & Aldrich dates to 1913 and uses brick laid in Flemish bond, punctuated by large multi-paned windows. A meticulous restoration was completed in 1992.

5. 
820 Fifth Avenue

One of the city’s grandest apartment buildings, this 12-story limestone palazzo has only one apartment per floor. Designed by Goldwin Starrett and Joseph Van Vleck for Fred T. Ley and Company and erected in 1916, this was one of the town’s earliest luxury apartments. Four-time governor Alfred E. Smith lived here, where he enjoyed nightly walks in the Central Park Zoo just across the avenue. Each of the twelve floors contain just a single apartment and the units rarely change hands - if one comes on the market expect to bring about $25 million with you to move in. 

WALK INSIDE THE PARK AT 64TH STREET. 

6. 
The Arsenal
64th Street at Fifth Avenue

Originally designed to resemble a medieval castle, The Arsenal is the second oldest building in Central Park, (the oldest being the Block House constructed in 1812 and tucked away in the northern reaches of the park). It was raised between 1847 and 1851 and was originally designed by architect Martin E. Thompson as a munitions depot for New York State’s National Guard. Despite not being included in the original plans for the park and battered by numerous critics, the versatile building has done duty as a police precinct, a museum (the precursor to the American Museum of Natural History), a weather bureau and an art gallery. It also served as a makeshift zoo until 1871. Taken over by public works czar Robert Moses in 1934, it was converted into his command center and remains the office of the Parks Commissioner to this day. Behind the arsenal is the Central Park Zoo, for which it serves as offices.

CROSS FIFTH AVENUE AND WALK DOWN 64TH STREET. 

7. 
Edward Berwind Mansion
828 Fifth Avenue

When this residence was built in the 1890s Edwin Berwind was America’s largest owner of coal mines. He helped fund the New York subway system and his coal powered the United States Navy during World War I. His was not only a prominent presence on Millionaires Row here but in Newport, Rhode Island where the Elms was built as his summer home. For this showcase Berwind hired Nathan Clark Mellen and when it was finished, he retained the Parisian decorating firm of Jules Allard’s to furnish its 18,000 square feet in a lavish 18th-century décor.

8. 
Wildenstein Gallery
19 East 64th Street

The gallery was founded in Paris some 130 years ago by Nathan Wildenstein who elected to leave his native Alsace in the wake of the Franco-Prussian War in order to remain a French citizen. The business he created in the 1870s has grown into a vast, far-flung enterprise that today includes galleries in New York and Tokyo and a research institute in Paris. Realizing that the market with the most potential was in the United States, in 1903 Wildenstein and his associates Ernest and René Gimpel opened a gallery on Fifth Avenue. In 1932 Wildenstein & Co. relocated to this elegant five-story limestone Beaux Arts-inspired space created by celebrated Philadelphia architect Horace Trumbauer that today serves as the company’s headquarters. 

RETURN TO FIFTH AVENUE AND TURN RIGHT. 

9. 
Temple Emanu-El
840 Fifth Avenue, northeast corner of 65th Street

This is the largest house of Jewish worship in the world. During the time of the American Revolution there were approximately 10,000 Jews living in the United States. Following the failure of the liberal revolutions in central Europe int he 1830s and 1840s, some 250,000 Jews from the regions of Germany and Austria streamed across the Atlantic. With a congregation of 37 Jews from Germany, Temple Emanu-El held its first services in a second floor loft at the corner of Grand and Clinton streets on the Lower East Side in 1845. By l868 the congregants built an edifice at Fifth Avenue and East 43rd Street, which was at that time the largest synagogue structure in America. This colossal temple dates to 1929. 

TURN RIGHT ON EAST 66TH STREET. 

10.      
Grant House
3 East 66th Street

This was the home of Ulysses S. Grant from 1881 to 1885. Forced into bankruptcy after a scandal-ridden presidency and ravaged by cancer, Grant retired here to concentrate on penning his memoirs. After his death, his autobiography met with great critical acclaim and earned a tidy sum for his family. It is still considered the best work of its type by an ex-President.

RETURN TO FIFTH AVENUE AND TURN RIGHT.

11.
Frick Collection
1 East 70th Street, northeast corner of Fifth Avenue

The mansion of coke and steel tycoon Henry Clay Frick swallows an entire block of some of the world’s costliest real estate. The mansion of Indiana limestone was designed by Thomas Hastings who also did the New York Public Library, and planned from the start as both home and gallery. Frick, once chairman of Carnegie Steel, was an avid collector of art, especially from the Italian Renaissance. He left the 1914 house and the art to the City, and the Frick Collection is one of the jewels of New York City’s art scene.

TURN RIGHT ON EAST 73RD STREET.

12.      
Joseph Pulitzer House
11 East 73rd Street

Stanford White designed this Venetian-inspired house for powerful newspaper publisher Joseph Pulitzer in 1903. Despite gobbling up as much expensive New York frontage as you will see on the Upper East Side, Pulitzer rarely lived in this house because of his extreme sensitivity to sound. At one time, it contained a special soundproof room (mounted on ball bearings to prevent vibrations).

RETURN TO FIFTH AVENUE AND TURN RIGHT.

13.    
1 East 75th Street, northeast corner of Fifth Avenue

On the verge of bankruptcy early in his career, John D. Rockefeller was staked with critical dollars by Stephen V. Harkness. That $70,000 investment of faith turned into many millions of dollars as Harkness became Rockefeller’s wealthiest partner in Standard Oil. His son Edward inherited much of the money and built this mansion on designs by a young architect, James Gamble Rogers. This reserved Roman-influenced mansion of Tennessee marble with granite and terra cotta trim, launched his career as one of America’s great academic architects for Yale, Columbia, Northwestern and others. In 1918, the building became the headquarters of the Commonwealth Fund, a foundation set up by Mrs. Stephen Harkness. 

14.
James B. Duke House
1 East 78th Street

This enormous freestanding house, modeled on the 18th-century Château Labottiére in Bordeaux, France is one of the most magnificent mansions in New York. It was built originally as the James B. and Nanaline Duke home in 1912, designed by Horace Trumbauer. Duke was born a poor boy in North Carolina and eventually rose to become a figure of unrivaled power in the American tobacco industry. Nanaline Duke and her daughter Doris gave the mansion to New York University in 1957, and it has been successfully adapted for use as the university’s graduate school of art history. 

15.
Payne Whitney House
972 Fifth Avenue

At their marriage in 1902 Payne Whitney and Helen Hay received as a present a Fifth Avenue plot with a house to be designed by Stanford White. This gift was not from Whitney’s father, William C. Whitney, who had made millions in street railways -- the son had quarreled with the father on the latter’s remarriage after the death of his first wife, Payne Whitney’s mother. Rather, the new house was the gift of Payne Whitney’s uncle, Oliver Hazard Payne, childless and with millions of oil refining dollars. A Civil War officer, Payne had early in life been cured of a serious disease by a physician and when he became wealthy much of his money was funneled to Cornell’s Medical College and others. The price tag for the granite mansion and furnishings topped a million dollars and kept climbing but fabled architect White, slain in a notorious murder by jealous romantic rival Harry Thaw in 1906, never saw its completion. Today the building serves as the French Embassy’s Cultural Services Office. 

16.  
Isaac and Mary Fletcher Mansion
2 East 79th Street at Fifth Avenue

In 1898 Isaac Fletcher, a banker and railroad investor, commissioned the famous Minnesota architect Cass Gilbert to build a house using William K. Vanderbilt’s French Renaissance chateau in the Blue Ridge Mountains, the Biltmore, as a model. Fletcher was so pleased with his new home that he hired Jean Francois Raffaelli to paint a portrait of it; the painting, the mansion and the Fletcher’s extensive art collection were all eventually bequeathed to the Metropolitan Museum of Art in 1917. Harry F. Sinclair, the founder of the Sinclair Oil Company and perpetrator of the Teapot Dome Scandal in the 1920s, purchased the Fletcher Mansion in 1920 and sold it in 1930 to Augustus Van Horne Stuyvesant, Jr., a descendant of New York pioneer Peter Stuyvesant. Today you can find the Ukrainian Institute of America here.  

17.
Duke-Semans Mansion
1009 Fifth Avenue

In 1901, Benjamin Duke, using American Tobacco money, bought this French Renaissance mansion on “Millionaire’s Row” as a speculative property. Various Duke family members lived in the house over the years and in 2006 it sold for $40 million, considered to be the highest-priced townhouse sale in Manhattan history.

18.
Metropolitan Museum of Art
1000 Fifth Avenue at 82nd Street

More people visit the Metropolitan Museum of Art than any other New York cultural touchstone - to the tune of four million a year. There is plenty to see - the art collection is the largest in the country. Its architectural pedigree is first rank as well. Richard Morris Hunt, the first American to graduate from Paris’ influential ノcole des Beaux-Arts, did the central section in 1902 and the wings were added by the legendary shop of McKim, Mead and White. The museum was founded in 1870 by an act of the New York legislature and set came to Central Park a decade later. The High Victorian facade by Calvert Vaux and Jacob Wrey Mould still stands as the east wall of the Lehman wing.

19.
1040 Fifth Avenue

After the assassination of her husband in 1963 this is where Jacqueline Kennedy came to raise her children. She moved here because it was close to her sister Lee Radziwill and because she wanted daughter Caroline to go to school at Sacred Heart on 91st Street. She bought the entire 15th floor for $250,000. In 1996, after she died, it sold for $9.5 million. The apartment overlooks the large reservoir in Central Park that is now named for her.

20.
William Starr Miller residence
135 Central Park West

The six-story Georgian brick-and-limestone ornament was designed by John Carrère & Thomas Hastings in 1914 for banker William Starr Miller, but was more famously known after 1944 as the home of Grace Vanderbilt, the “Queen of America’s High Society.” The founder of the Vanderbilt fortune, Commodore Cornelius Vanderbilt, was a notorious tightwad, but he was also the richest man ever to die in America when he passed so his descendants had a bundle to build impressive homes. For nearly forty years, 1048 Fifth Avenue did not function as a mansion at all: it housed the collections of the Yidisher Visnshaftlekher Institut, now officially known as YIVO Institute for Jewish Research. 

21.
Solomon R. Guggenheim Museum
1071 Fifth Avenue, between 88th and 89th streets

The Guggenheims were a mining family who made their money in the Yukon Gold Rush of the 1890s. By that time Solomon, then in his thirties, was more interested in prospecting in the art world. He collected old masters and embraced 20th century modern art early on. In 1937, he established the Solomon R. Guggenheim Foundation to foster the appreciation of modern art. In the 1940s master architect Frank Lloyd Wright was hired to create a home for the “The Museum of Non-Objective Painting.” Wright was no fan of the New York streetscape; he claimed that his museum would make the nearby Metropolitan Museum of Art “look like a Protestant barn.” His ribbon-like design, loved by some and hated by others, would be his last major work when it opened in 1959. Solomon Guggenheim did not live long enough to see his collection displayed here - he died in 1949 at the age of 88.

22.
Andrew Carnegie Mansion/Cooper-Hewitt National Design Museum
2 East 91st Street

This was “the country” back in 1898 when steel baron Andrew Carnegie bought land far north of the bustle of the city, a place where he could puddle around in one of Manhattan’s few private gardens. Carnegie was in the process of selling his United States Steel to J.P. Morgan for $400 million and was looking for a retirement house from which he could give away all his money, much of it to fund the building of more than 2,700 public libraries across the world; 39 of which were in New York City alone. Six of those would be designed by the architectural firm of George Fletcher Babb, Walter Cook, and Daniel W. Willard who also did this 64-room Georgian manor intended to be the“most modest, plainest, and most roomy house in New York.” Today the mansion trundles on as the Cooper-Hewitt National Design Museum, a branch of the Smithsonian Institution that is America’s only museum devoted exclusively to historic and contemporary design.  

23.  
Otto Kahn House/Convent of the Sacred Heart
1 East 91st Street, northeast corner of Fifth Avenue

In business German-born financier Otto Hermann Kahn was known for his knack of organizing American railroads. In the arts he was known for his patronage of the Russian ballet, the Paris Conservatory orchestra, and the Metropolitan Opera Company. Completed in 1918, after four years in the making, on Italian Renaissance plans drawn by J. Armstrong Stenhouse and Charles Pierrepont Henry Gilbert, his enormous 80-room house was one of the largest in America. After Kahn died in 1934 at the age of 67 the mansion was acquired for use as a school by the Society of the Sacred Heart in 1934. 

TURN RIGHT ON EAST 91ST STREET. TURN RIGHT ON PARK AVENUE.

24.
Church of St. Ignatius Loyola
980 Park Avenue, southwest corner of 84th Street

This parish organized in 1851 as the St. Lawrence O’Toole Church, taking the name of a 12th century Dublin bishop. The congregation was assembling in a modest wooden structure the following year and a humble brick meetinghouse the year after. A name change accompanied the coming of this limestone house of worship in 1898 from a design by William Schikel. The German-American architect had an even grander vision for St. Ignatius of Loyola but the dueling 210-foot towers were never built. The church was the site of Jacqueline Kennedy’s funeral in 1994. 

TURN RIGHT ON EAST 75TH STREET. 

25.  
Whitney Museum of American Art
945 Madison Avenue, southeast corner of East 75th Street

Gertrude Vanderbilt Whitney, a great-granddaughter of the Vanderbilt family money, was a sculptor of some renown in her own right, but it is her art collection and the museum it spawned that carries her legacy. Hungarian-born architect Marcel Breuer created the granite landmark in 1966 that is the third home for the Whitney Museum of American Art.

RETURN TO PARK AVENUE AND TURN RIGHT.

26.  
Asia Society
725 Park Avenue, northeast corner of70th Street

The Asia Society was founded by John D. Rockefeller III in 1956 to foster better relations between America and Asia through culture and the arts. Its galleries are worth a look. The Society’s New York headquarters exhibits the Rockefeller Collection of Asian Art which includes some of the most important masterpieces from the Far East.

TURN LEFT ON EAST 70TH STREET.

27.  
Paul Mellon House
125 East 70th Street, between Park and Lexington avenues

Many consider East 70th to be the finest of all New York City streets. This townhouse was built in 1965 for billionaire philanthropist Paul Mellon who demolished two 1860 roughhouses for his 40-foot-wide stuccoed French provincial mansion. When it went on the market in 2005 the price tag was $26.5 million.

RETURN TO PARK AVENUE AND TURN LEFT.

28.  
Union Club
701 East 69th Street at Park Avenue

Organized in 1836, the Union is considered the first men’s social club in New York, or at least the oldest. Club members were famously conservative. During the Civil War, seceding from the Union did not disqualify members from the Union Club -  Confederate members were not expelled during the rebellion. This is the sixth clubhouse for the venerable organization, the third constructed by the club. The rusticated limestone confection under a mansard roof, designed by William Adams Delano and Chester Holmes Aldrich is so big it looks like a Fifth Avenue mansion on steroids. When the Union Club took residency in 1933 the membership roster numbered 1,300 and the club humidor was home to 100,000 cigars.

29.  
Percy Rivington Pyne House/America’s Society
680 Park Avenue

Percy Rivington Pyne II was the grandson of Moses Taylor, founder of the First National City Bank of New York and a stockholder in the Delaware, Lackawanna and Western Railroad. Pyne would trot in his grandfather’s footsteps in his business career. He moved his family into this Colonial Revival townhouse in 1909 from McKim, Mead & White when he was 52 years old. It later became the Soviet Mission to the United Nations; Nikita Khrushchev stayed here while visiting the United Nations. The Marquesa de Cuevas purchased the building to save it from demolition and, in 1966, donated it to the Americas Society, then known as the Center for Inter-American Relations. Founded in 1965 by a group of businessmen led by David Rockefeller, the Center for Inter-American Relations became the Americas Society in 1985.

30.  
Harold Pratt House
58 East 68th Street, southwest corner of Park Avenue

This elegant town house took its place among Upper East Side mansions in 1920 as the home for Harold Irving Pratt. His father’s Astral Oil was folded into John D. Rockefeller’s Standard Oil of New Jersey colossus which insured the family fortune. The house which was officially opened as the Council of Foreign Relations’ new headquarters on April 16, 1945.

TURN RIGHT ON 65TH STREET.

31.  
Roosevelt House
47-49 East 65th Street

Roosevelt House, a double townhouse, was a wedding gift from Sara Delano Roosevelt to her son, Franklin, and his new bride, Eleanor. Sara lived at No. 47, and the young couple at No. 49. At Roosevelt House, Franklin began his storied political career, rising from New York State Senator and Assistant Secretary of the Navy to Governor of New York and President of the United States. Here he also renewed his strength and optimism after polio left him unable to walk. 

CONTINUE ON TO FIFTH AVENUE AT CENTRAL PARK. TURN LEFT TO RETURN TO THE TOUR STARTING POINT.