The 14 Most Stunning Architectural Gems on New York’s Fifth Avenue

There are many buildings that stun in the Manhattan skyline, but nothing dazzles quite like the city’s fabled Fifth Avenue. Known as the spine of Gotham, this one street—stretching from Greenwich Village to Harlem—is being celebrated in a new book from Monacelli called Fifth Avenue: From Washington Square to Marcus Garvey Park by William J. Hennessey, which is out October 5. The book is a follow-up to the author’s 2020 hardcover, Walking Broadway, an architectural tour of the busy street. Fifth Avenue is an illustrated guide that takes readers along the breadth of Fifth Avenue through six fact-filled walking tours, with architecture tidbits, block by block.

It covers iconic landmarks like the Washington Square Arch in Greenwich Village—built to commemorate the centenary of George Washington’s 1789 inauguration as president—to the Empire State Building and the Flatiron Building, as well as lesser-known places, like the Engine Company 14, the Morton Plant House, and the fabled Charles Scribner’s and Sons. Fifth Avenue is home to architectural gems designed by Bjarke Ingels, Rem Koolhaas, and Frank Lloyd Wright, and they’re all covered in Hennessey’s book, with detailed maps, historic illustrations, and new photos.

Below, AD surveys 14 buildings highlighted in the book to make your next saunter down Fifth Avenue all the more memorable.