The Fifth Avenue Hotel, across from Madison Square Park, following an 1899 snowstorm. "The Fifth-Avenue Hotel has borne a conspicuous part in the public life of the metropolis, and has been identified with the most notable local events of the generation since its opening, in 1859. The house fronts upon Madison Square, the most charming of the smaller parks of the city, at the junction of Broadway and Fifth Avenue the two great thoroughfares. It is unequalled in the number and spaciousness of its corridors, halls, and public rooms, and the commodious character of its guest rooms." This description by King's Handbook of New York (1893) demonstrates The Fifth Avenue Hotel's luxurious reputation. When Amos Eno built the hotel in 1859, the neighborhood was still dominated by town houses and it was thought to be so far uptown that it was called "Eno's Folly." Luxurious touches including a fireplace in every bedroom, private bathrooms, lavish public rooms, an Otis elevator and four hundred servants and fifty conveyances standing ready to serve the hotel's 800 guests, compensated for its location and assured its success. The hotel was razed in 1908, ahead of the construction of the Toy Center Building on the same site.

Caleb Smith, a librarian at Columbia University, walked the entirety of Broadway in the summer of 2001: from 262nd Street in the Bronx to Battery Park at the southern tip of Manhattan. The photographs, taken during the walk, capture his view of Broadway, New York's uncompromising main street. (He was later inspired to walk every street in Manhattan, which he did over a two-year period between 2002 and 2004.) This walk is a "best of" Caleb's Broadway expedition.

Dewey Arch ca. 1899 This wood-and-plaster arch and colonnade at Madison Square was the focal point of Commodore George Dewey's triumphal procession through New York City on September 30, 1899, after defeating the Spanish forces at Manila Bay on May 1, 1898. The temporary construction, erected by the National Sculpture Society under the leadership of architect Charles R. Lamb and sculptor Frederic W. Ruckstall, was completed on September 29, just one day before the procession. The arch was intended to attract subscriptions for a permanent structure, but Dewey's popularity waned and the project was abandoned. The heavily deteriorated temporary monument was removed in late 1900.

On February 11th, 1899, a blizzard known as the Great Arctic Outbreak moved across the United States, reaching as far as Florida, New Orleans, and even Cuba. In New York City, the average temperature was −6 °F and Central Park saw 16 inches of snow, with other areas measuring a record 2-3 feet.

International Toy Center, ca. 1916 Construction began on the beguilingly named International Toy Center in 1908 and was completed the next year. It had large shoes to fill, as it replaced the famed Fifth Avenue Hotel, one of the first (but hardly the last) of New York's luxury hotels. Moreover, the building showed the speed at which the city was industrializing; only 70 years before, this area had been farmland. Though initially named the Fifth Avenue Building, it earned its new moniker during the First World War when scarcity in European manufactures caused a boost in the toy industry. By the end of the following World War, many of the industry's largest players inhabited the building and in the 1960s manager Helmsley-Spear restricted the leases to toy companies. By the early 1980s, 95% of toy transactions in the United States were handled by the complex's 600 toy tenants (by then the Toy Center comprised two buildings). Though a series of sales and changing markets left the building partly unoccupied during the early 2000s, 200 Fifth Avenue now hoasts Eataly, Tiffany, and many others.