Opened in 1904 by John Jacob Astor as a companion to the original Waldorf-Astoria (at the time 20 blocks south), the lavish Trowbridge & Livingston-designed hotel was no stranger to controversy. Its location opposite the mansions of the Vanderbilts and the Rockefellers, led to many lawsuits and much rancor.

Though located on the same plot as a previous hotel, the Plaza, made famous by Eloise, was completed in 1907. Designed by Henry Hardenberg, it was heralded as "the greatest hotel in the world" upon its opening, throwing a lavish celebration and quickly earning a reputation as a haunt of the rich and famous.

The McKim, Mead, & White-designed Savoy-Plaza Hotel was built as a companion to the Plaza Hotel across Fifth Avenue and quickly earned its name as another luxury hotel. However, after a sale to Hilton and a period of decline, it eventually was sold and demolished, despite fervent opposition from preservationists.

Though perhaps not as famous as its some of its neighbors, the Sherry-Netherland has part of the city's past incorporated into its structure. Replacing the Hotel New Netherland, which had occupied the lot since 1890, the Sherry-Netherland was completed in 1929, the same year as the neighboring Vanderbilt Mansion was demolished. Because of this timing, many of the hand-carved friezes and marble works from the Vanderbilt home were included in the Sherry-Netherland's lobby.

Dissatisfied with the "democratization of public manners," French restauranteur Charles Pierre Casalasco organized a group of financiers to build a hotel. The 41-story Hotel Pierre resulted, earning a reputation for grandeur that its founder delighted in.

The youngest hotel on this walk, the Park Lane Hotel was completed in 1971. Built by the Helmsleys, the Emory Roth & Sons design is an important modern/postmodern addition to the neighborhood. Its facade includes slender black windows spanning the entire 44 stories in vertical stripes. Despite its modern design, the Park Lane Hotel embodies the spirit of the other hotels on this walk, attempting to secure a high-end clientele by providing a luxurious experience.

The Emery Roth-designed Hotel St. Moritz quickly gained a popularity akin to the chic Swiss vacation town it was named after. A favorite of athletes and theatrical types, author W. Parker Chase described it as "a picturesque cliff, amidst towering trees to the north, and other soaring skyscrapers to the south."

The 38-story Art Deco Barbizon Plaza Hotel opened in 1930. Attempting to attract musicians and artists, the Barbizon offered studios, soundproofed practice rooms, and performance spaces! Though it had multiple owners, its earned some notoriety when Donald Trump purchased it along with 100 Central Park South, attempting to tear them down and build a new tower. However, Trump's attempts to evict rent stabilized and controlled tenants through a campaign of harassment failed, and the towers remain.