361 Fifth Avenue was designed c. 1906 by Trowbridge & Livingston as the uptown flagship location of the B. Altman & Company department store. After remaining at 18th Street & 6th Avenue for 30 years, Altman moved their store uptown after the popularity of the Ladies’ Mile ended. After the department store closed, the building was converted for academic use where it holds the CUNY Graduate Center and a branch of the New York Public Library.

100 West 33rd Street was designed c. 1910 by Daniel H. Burnham & Company for the Gimbels department store. The New York flagship received considerable attention as the site of the 1939–40 sale of art and antiquities from the William Randolph Hearst collection.

1293 Broadway was designed c. 1902 by Buchman & Fox as a store for Saks & Company. When Horace Saks decided to build a new store on 5th Avenue in 1924, he sold the entire operation to Bernard Gimbel. The old building here became a division of the adjacent Gimbels, with a bridge connecting it, and was renamed Saks 34th Street. In 1965, the exterior was reclad to become a branch of E.J. Korvette, a discount department store. In 1985, the interior was gutted to become a vertical indoor shopping mall.

Designed c. 1902 by Charles L. Berg, 316 Fifth Avenue was home to Kaskel & Kaskel. The store was a leading haberdashery at the turn of the century, providing shirts for the city’s wealthiest gentlemen. In 2018, the building was demolished to be replaced with a residential tower designed by FXFOWLE.

620 Sixth Avenue was designed c. 1897 by DeLemos & Cordes as the largest store building in the world, for Henry Siegel, president of the successful Chicago department store Siegel, Cooper & Co. It originally had a fountain in the central atrium which boasted a large statue by Daniel Chester French. Saying "Meet me at the fountain" was a common catchphrase for shoppers along Ladies' Mile. The store also offered both a dentist and doctor office, a beautician and a barber shop, a post office, an office for theatre tickets and a bank. The building served as a the Greenhut Hospital during WWI for military personnel, and had been used primarily for warehouse space until being converted for retail use.

335 Fifth Avenue was designed c. 1890 by Renwick, Aspinwall & Russell as a showroom for A.T. Demarest & Co., a high-end carriage manufacturer.

Founded as Young's Stetson Hats in 1911, JJ Hat Center opened as one of the 50 or so upscale men's milliners that dotted New York City. In the 1960's, the company moved into its current location at 310 5th Avenue which was originally a showroom for IBM.

135 West 18th Street was designed c. 1896 by Kimball & Thompson as a stable for the B. Altman Company's dry goods store next door.

881 Broadway was designed c. 1868 by Griffith Thomas as a department store for the prominent dry-goods company Arnold Constable. When it expanded to Fifth Avenue in 1876, it was said to be "one of the largest business establishments in the world". In 1914, the store was closed and the business moved uptown to Fifth Avenue and 40th Street. In 1915, the whole complex was converted for use as a wholesale store.

901 Broadway was designed c. 1869 by James H. Giles as a department store for Lord & Taylor. This was their third location, quickly growing and moving uptown as business interests centered around Union Square. The firm continued to expand over the years, eventually occupying most of the buildings on the block bounded by Broadway, Fifth Avenue, and East 19th and 20th streets. Lord & Taylor moved uptown to Fifth Avenue between 38th and 39th Streets in 1914.

889 Broadway was designed c. 1883 by Edward Hale Kendall as a store and apartment building with two stories of retail space for the Gorham Manufacturing Co., one of the nation's leading manufacturers of fine silver at the end of the 19th century. Gorham later took over the entire building for their operations. In 1905, the Gorham Company moved uptown to 36th Street.

Built on part of the former Clement Clarke Moore estate. The estate had extended from what is now 19th Street to 24th Street, and from Eighth Avenue to the Hudson River. On a hill, between today’s 22nd and 23rd Streets, sat the family mansion—a three-story, hipped roof residence above an deep English basement. As the city inched closer to Moore’s expansive property, he divided his land into building lots and in 1818 donated a large portion for the construction of the General Theological Seminary. The manor house would survive a few more years—long enough for Clement Clarke Moore to write “The Night Before Christmas” there on December 23, 1822.

Cushman Row was built in 1840 by Don Alonzo Cushman, bringing to fruition Clement Clarke Moore's genteel ambitions for Chelsea. This is one of the nation's finest and best preserved uniform rows of Greek Revival houses, second in New York only to Washington Square's. Its graciousness is enhanced by front gardens occupying setbacks prescribed for the purpose by Clement Clarke Moore. These complement the lush Seminary grounds across the street and make this block one of the city's loveliest.

Chelsea Court was designed c. 1920 by C.P.H. Gilbert for Cushman family interests. Chelsea Court’s grand entrance hints at what its architect C.P.H. Gilbert is best known for: Gilded-Age urban mansions like Fifth Avenue’s Warburg House, now part of the Jewish Museum. The separate apartment building to the left was clearly part of Gilbert’s Chelsea Court design. The gated alley between them leads to Chelsea Court’s rear lawn, a kind of secret garden hidden in the center of the block behind the rowhouses on 20th and 21st Streets.

The first iteration of London Terrace was designed c. 1845 by Alexander Jackson Davis as a series of elegant rowhouses for Cyrus Mason and William Torrey on part of the former Moore estate. The residences filled with well-to-do merchant class families and their domestic staff. Former residents included Catherine Underhill, John G. Plimpton, John P. Brown and Richard Douglas. In 1929, the block was demolished and replaced with the current apartment structure which was designed by Farrar & Watmough.

Former mansion of financier Leonard Jerome which was designed c. 1857 by Thomas R. Jackson. Jennie Jerome Churchill, Winston Churchill's mother, grew up here. After being unable to find a buyer in the 1960's the formerly-landmarked home was demolished and replaced with the Merchandise Mart building.

436 West 22nd Street was built c. 1835 for James Coggill who was a successful actor. In 1839, it was purchased by Edwin Forrest who was one of America's best-known actors. Forrest also had a country house in Yonkers.

Designed c. 1907 by McKim, Mead & White as a clubhouse, 120 Madison Avenue was originally built as the Colony Club, the first social club established in New York City by, and for, women. The interior was decorated by Elsie de Wolfe. During World War I, the original clubhouse was used first as a convalescent hospital, then as a nurses’ mobilization center. It was then taken over by the new Carroll Club for Catholic girls. In 1963 the building was purchased for about $500,000 by the American Academy of Dramatic Arts which still occupies it today.

Designed by T. Thomas & Son, the first location of the Union Club of the City of New York stood on the northwest corner of Fifth Avenue and 21st Street until about 1903. Italianate in design, this free-standing threestory structure resembled the Travelers (1830) and Reform Clubs (1837) in London. They relocated to the northeast corner of Fifth Avenue and 51st Street, in a limestone clubhouse occupied from 1903 to 1933.

15 Madison Square North was home to the Columbia University Club which was incorporated to further interests of alumni of Columbia University with its own facilities and programs.

Daly's New Fifth Avenue Theater stood at 27-31 West 28th Street; sometimes referred to as 1185 Broadway.

On this site, in 1869, Edwin Booth opened a grand theatre to a design by Renwick & Sands in the Second Empire style.

The original Madison Square Garden was designed c. 1889 by McKim, Mead & White as an upscale event venue. At the time, it was considered the largest entertainment hall in the world. In 1906, Stanford White was shot and killed here by Harry Thaw over a relationship dispute.

Former Episcopal Church of the Holy Communion, a neo-Gothic church complex which was designed by Richard Upjohn. The church remained a house of worship until 1975 when the congregation merged with two nearby parishes. Edith Wharton was married here.

When opened in 1888, the Everard Baths were considered some of the finest Turkish bath in the world. Its opulent decoration included frescoes, marble walls, and stained glass.

In 1898, Henri and Louis Mouquin leased the old Knickerbocker Cottage and rechristened it Mouquin's Cafe de Bordeaux, an upscale French restaurant. In 1868, the New York Athletic Club had been founded on this site.

Completed in 1859 by Amos R. Eno, the Fifth Avenue Hotel at 200 Fifth Avenue, whose gleaming white-marble housed 100 apartment suites, was the first American hotel with an elevator and private bathrooms, as well as a fourth meal, or "late supper", and was a popular meeting place for politicians, brokers and speculators. It was one of the most luxurious in New York City at the time. Because of its opulence, as well as its location at the far uptown edge of the city, it was dubbed "Eno's Folly". The site previously had been an inn where travelers leaving the city or returning to it could get a meal or lodging before continuing their trip. The hotel stood between East 23rd and East 24th Streets facing Madison Square, where the Toy Center South would later stand.

First location of the Waldorf-Astoria Hotel which was designed c. 1893 by Henry J. Hardenbergh for William Waldorf Astor. The hotel was later joined with his cousin John Jacob Astor IV's half-block Astoria Hotel in 1897. The two buildings combined for 1,300 guest rooms and 40 public rooms. It was demolished in 1929 for the Empire State Building and relocated uptown on Park Avenue.

Designed c. 1904 by John H. Duncan for William C. Dewey with an opulent Louis XVI–style lobby with an ornate high ceiling, mirrored panels, stained glass, marble pillars, and incredible chandeliers. It served as the long-term residence of Isadora Duncan, Henry Miller, Edith Wharton, and Doris Duke, and was the location of Fiorello La Guardia’s inaugural ball in 1938.

1200 Broadway was designed c. 1872 by Stephen Decatur Hatch as a luxurious hotel for Peter Gilsey. Its bar, made of silver dollars, was a popular gathering spot for the elite as well as celebrities of the time like Mark Twain and Oscar Wilde.

The Prince George Hotel was designed c. 1905 by Howard Greenley for Charles Rogers as an upscale hotel with opulent ballrooms for entertaining.

1232 Broadway was designed c. 1868 by Henry Engelbert for Ellias S. Higgins as a residential hotel that offered shared services for long-term visitors. By the 1870's, it used as a guest hotel under the management of Henry Milford Smith. It is now known as the Clark Apartments after being converted for residential use.

49 West 32nd Street was designed c. 1911 by Henry J. Hardenbergh for William R. H. Martin as the luxurious Hotel Martinique. The Martinique maintained a number of different restaurants and entertainment rooms, including a dining room that was modeled after the Apollo Room in the Louvre.

50 West 34th Street was designed c. 1913 by F. M. Andrews & Co. for General Edwin A. McAlpin. It was built at a cost of $13.5 million and was the largest hotel in the world when opened. There were floors restricted to women, men and even night workers - where silence was enforced during the day. There was a tapestry gallery, a banquet room with a vaulted ceiling, a giant marble lobby, a Louis XVI-style dining room and Russian and Turkish baths.