Skyscrapers weren’t always the shimmering glass-and-steel giants we know today. In the late 19th century, the idea of building upward wasn’t just a necessity. It was a statement. Cities were swelling, land was expensive, and new engineering feats made it possible to defy traditional limits. The first skyscrapers were bold, intricate, and unapologetically grand.
Many of these pioneering structures still stand, their ornate facades and groundbreaking foundations a reminder of where it all began. Here’s a look at the ten oldest skyscrapers in the world, the buildings that first reached for the sky.
1. Ames Building, Boston, Massachusetts (1893)
Nestled at 1 Court Street in Boston, Massachusetts, the Ames Building stands as a testament to the city’s architectural evolution. Completed in 1893, it was designed by the esteemed firm Shepley, Rutan, and Coolidge in the Richardsonian Romanesque style. At fourteen stories, it was Boston’s tallest building upon completion and is considered the Beantown’s first skyscraper.
Commissioned by industrialist Frederick Lothrop Ames, the building showcases a façade adorned with granite and sandstone, featuring grand arches and intricate carvings. Its construction marked a significant achievement as the second-tallest masonry load-bearing wall structure globally at the time, surpassed only by Chicago’s Monadnock Building.
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Over the years, the Ames Building has undergone several transformations. Initially serving as office space, it was converted into a luxury boutique hotel in 2009. In 2020, Suffolk University acquired the building, repurposing it as a student residence hall.
Visitors to the Ames Building can appreciate its historical significance and architectural grandeur. Situated adjacent to the Old State House and near Faneuil Hall, its location offers a rich blend of Boston’s past and present. While the interior now serves as student housing and is not open to the public, the building’s exterior remains a visual delight for architecture enthusiasts and history buffs alike.
2. Manhattan Building, Chicago, Illinois (1891)
Located at 431 South Dearborn Street in Chicago, Illinois, the Manhattan Building was designed by architect William Le Baron Jenney and constructed between 1889 and 1891. Upon its completion, the 16-story structure was the tallest building globally and is recognized as the oldest surviving skyscraper with a purely skeletal steel frame.
The building’s distinctive design features bow windows that enhance natural light within its interior spaces. The façade combines a granite base for the lower floors with brick on the upper stories, reducing the load on the internal steel framework. This innovative approach addressed concerns about wind-induced sway, with Jenney incorporating structural elements to ensure stability.
Today, the Manhattan Building continues to serve as a commercial office space, retaining its historical significance and architectural charm. Visitors and architecture enthusiasts can admire its exterior, which showcases the early adoption of steel-frame construction—a pivotal development in skyscraper design. Situated in Chicago’s Loop neighborhood, the building is part of the historic Printing House Row District, offering a glimpse into the city’s rich architectural heritage.
The interior is primarily occupied by businesses and may not be accessible to the general public.
3. Old Chronicle Building, San Francisco, California (1889)
The Old Chronicle Building, also known as the de Young Building, is a historic landmark located at 690 Market Street in San Francisco, California. Completed in 1889, it was designed by the renowned Chicago architectural firm Burnham and Root in the Richardsonian Romanesque style. At the time of its completion, the ten-story building, featuring a clock tower reaching 218 feet, was the tallest structure on the West Coast and is considered San Francisco’s first skyscraper.
Commissioned by M. H. de Young, owner of the San Francisco Chronicle, the building served as the newspaper’s headquarters and was a prominent feature of the city’s “Newspaper Row,” sharing the area with other major publications. In 1905, during a mayoral victory celebration, fireworks ignited the wooden clock tower, leading to its removal. Despite suffering significant damage during the 1906 earthquake and subsequent fires, the building was rebuilt under the supervision of architect Willis Polk, preserving its historical significance.
Over the years, the Old Chronicle Building underwent several transformations. In 1962, an attempt to modernize its appearance led to the original masonry façade being covered with a contemporary exterior. However, in 2004, efforts were made to restore its historic character, and the building was converted into the Ritz-Carlton Club and Residences.
Today, visitors can admire the restored façade that reflects the building’s original 19th-century design. While the interior now houses private residences and is not open to the public, the exterior stands as a testament to San Francisco’s resilience and commitment to preserving its historical landmarks.
4. New York Times Building (41 Park Row), New York City (1889)
The building at 41 Park Row in Manhattan holds significant historical importance as the former headquarters of The New York Times. Completed in 1889, it stands as a testament to the newspaper’s early prominence and the architectural innovation of its era.
The New York Times was founded in 1851 and initially operated from 113 Nassau Street. As the newspaper’s influence grew, it relocated to a newly constructed building at 41 Park Row in 1858, making it the first structure in New York City designed specifically for a newspaper. By the late 1880s, to accommodate its expanding operations, the Times commissioned architect George B. Post to design a larger Romanesque Revival-style building on the same site. This new 13-story structure was completed in 1889, showcasing advanced construction techniques of the period.
The 1889 building featured a façade adorned with intricate stonework and large arched windows, reflecting the Romanesque Revival style. Its construction was notable for being executed around the existing operations of the newspaper, allowing The New York Times to continue publishing without interruption. This engineering feat demonstrated innovative building practices of the time.
In 1905, The New York Times relocated to a new building at One Times Square, and 41 Park Row underwent modifications, including the addition of four stories. Pace University acquired the building in 1951, repurposing it for academic use. The structure has since been designated a New York City landmark and contributes to the Fulton–Nassau Historic District.
Today, 41 Park Row serves as an academic building for Pace University. While interior access is primarily for university purposes, visitors can appreciate the building’s historical façade and its role in New York City’s rich journalistic and architectural heritage.
5. Wilder Building, Rochester, New York (1888)
Constructed between 1887 and 1888, this eleven-story structure is considered Rochester’s first modern skyscraper and remains one of the oldest early skyscrapers in the United States.
Designed by the prominent Rochester architectural firm Warner & Brockett, the building showcases a modified Romanesque style. Its original design featured spires at each corner of the roof, which have since been removed.
A notable feature of the Wilder Building is its association with the invention of the mail chute. James Goold Cutler, who received U.S. Patent 284,951 on September 11, 1883, for the mail chute, installed a perfected version in the Wilder Building during its construction. With the demolition of the Elwood Building in 1965, the Wilder Building’s mail chute is currently the oldest surviving example of this innovation.
Today, the Wilder Building continues to serve as a functional office space, housing various businesses and organizations. Its prime location at the Four Corners in downtown Rochester makes it a central and accessible hub for commerce.
Visitors and architecture enthusiasts can appreciate the building’s historical significance and its role in shaping Rochester’s skyline. While interior access may be limited due to its use as private office space, the exterior offers a glimpse into the city’s rich architectural heritage.
6. Rookery Building, Chicago, Illinois (1888)
Nestled at the corner of LaSalle and Adams Streets in Chicago, the Rookery Building was completed in 1888 by the renowned partnership of Daniel Burnham and John Wellborn Root. This iconic structure seamlessly blends masonry and skeletal frame construction, marking a pivotal moment in the evolution of modern architecture.
The building’s name, “The Rookery,” harks back to a time when the site housed a temporary city hall teeming with crows and pigeons, as well as politicians, leading locals to dub it a “rookery.” Embracing this moniker, Root incorporated bird motifs into the building’s ornamental design, adding a whimsical touch to its grandeur.
One of the Rookery’s most captivating features is its central light court. Originally designed to flood the interior with natural light, this two-story atrium was reimagined in 1905 by the legendary Frank Lloyd Wright. Wright’s renovation introduced white Carrara marble, intricate Persian-inspired patterns, and elegant bronze chandeliers, transforming the space into a luminous blend of form and function.
Beyond its aesthetic appeal, the Rookery was an engineering marvel of its time. Root devised a “grillage foundation,” a network of iron rails encased in concrete, to support the building’s weight on Chicago’s challenging soil. This innovative approach ensured the structure’s stability and longevity.
Today, the Rookery Building continues to function as a vibrant office space, housing various businesses while welcoming visitors to explore its historic halls. Guided tours offer insights into its rich past, architectural nuances, and the visionary minds behind its creation. As a designated Chicago Landmark and a listing on the National Register of Historic Places, the Rookery remains a cherished emblem of the city’s architectural heritage.
7. Sun Building, Washington, DC (1887)
Nestled at 1317 F Street NW in Washington, DC, the Sun Building stands as a testament to architectural innovation and historical significance. Designed by Alfred B. Mullett, its construction spanned from 1885 to 1887, originally serving as the Washington bureau for The Baltimore Sun.
Upon completion, this nine-story edifice was among the city’s earliest skyscrapers, showcasing a steel-frame structure, a pioneering feature at the time. Its façade is adorned with sun motifs and sunflowers, an early example of corporate branding through architecture.
The building was equipped with steam-powered elevators, later upgraded to hydraulic systems in 1909 and electric elevators in 1922. In 1904, architect B. Stanley Simmons oversaw modifications for the American Bank, including the addition of a ninth floor in 1907 to accommodate the Interstate Commerce Commission’s hearing room.
Throughout its history, the Sun Building has housed notable tenants, including Woodrow Wilson’s law firm and the early offices of the Federal Bureau of Investigation under J. Edgar Hoover.
Recognized for its architectural and historical value, the Sun Building was added to the National Register of Historic Places on March 27, 1985.
8. Osborne Apartments, New York City (1885)
The Osborne Apartments, located at 205 West 57th Street in Manhattan, New York City, was constructed between 1883 and 1885, and stands as one of the city’s oldest luxury apartment buildings.
Designed by architect James Edward Ware, the Osborne showcases a Romanesque Revival style with a façade clad in rusticated brownstone. The building’s southern section facing 57th Street rises 11 stories, while the northern section extends to 15 stories. The interior is notable for its elaborate lobby, adorned with stuccoed and mosaic-tiled walls, reflecting the opulence of the Gilded Age.
Commissioned by stone contractor Thomas Osborne as a speculative investment, the building’s construction cost of $2 million led to financial difficulties, resulting in its acquisition by the Taylor family in 1889. Throughout its history, the Osborne has been home to numerous artists, musicians, and professionals, contributing to its reputation as a cultural hub. In 1991, it was designated a New York City landmark, and in 1993, it was added to the National Register of Historic Places.
Situated at the northwest corner of 57th Street and Seventh Avenue, the Osborne is directly across from Carnegie Hall and in close proximity to Central Park. This prime location places it within Manhattan’s “Billionaires’ Row,” a stretch known for its luxury real estate and cultural institutions.
Today, the Osborne operates as a cooperative residential building, maintaining its historic charm while offering modern amenities. Its enduring architectural beauty and cultural significance continue to attract residents and visitors alike, preserving its legacy as a quintessential New York City landmark.
9. Hotel Chelsea, New York City (1884)
The Hotel Chelsea, often simply referred to as the Chelsea Hotel, is a historic landmark located at 222 West 23rd Street in Manhattan, New York City. Constructed between 1883 and 1884, it was initially designed as one of the city’s first cooperative apartment complexes by architect Philip Hubert in a style described as Queen Anne Revival and Victorian Gothic. The 12-story red brick building, adorned with wrought-iron balconies, was, for a time, the tallest structure in New York City.
In 1905, the building transitioned into a hotel, quickly becoming a haven for artists, writers, musicians, and actors. Its bohemian atmosphere attracted a plethora of notable residents and guests over the decades. Literary figures such as Mark Twain, O. Henry, Arthur C. Clarke, and Jack Kerouac, who penned “On the Road” during his stay, found inspiration within its walls. The hotel also hosted musical legends like Bob Dylan, Jimi Hendrix, Janis Joplin, and Patti Smith. Andy Warhol filmed his iconic movie “Chelsea Girls” at the hotel in 1966, further cementing its status as a cultural landmark.
Throughout its history, the Chelsea Hotel has been a backdrop for both artistic creation and tumultuous events. The poet Dylan Thomas fell ill at the hotel before his death in 1953, and in 1978, punk rock musician Sid Vicious was implicated in the death of his girlfriend, Nancy Spungen, in one of its rooms.
In recent years, the hotel has undergone renovations to preserve its historic character while updating its facilities.
10. Temple Court Building, New York City (1883)
The Temple Court Building, located at 5 Beekman Street in Manhattan’s Financial District, is a remarkable example of late 19th-century architecture. Designed by Benjamin Silliman Jr. and James M. Farnsworth, the original structure was completed in 1883, showcasing a blend of Queen Anne, neo-Grec, and Renaissance Revival styles. Its distinctive red-brick façade, adorned with tan stone and terracotta accents, is complemented by two pyramidal towers at the corners.
In 1889, an annex was added to the building, designed solely by Farnsworth in the Romanesque Revival style. This addition features a limestone façade and seamlessly integrates with the original structure. A standout feature of the Temple Court Building is its nine-story atrium, crowned by a pyramidal skylight, which floods the interior with natural light and highlights the intricate iron railings and detailed ornamentation.
After a period of vacancy starting in 2001, the building underwent significant restoration and redevelopment. In 2016, it reopened as part of The Beekman Hotel and Residences complex. This project included the addition of a 51-story condominium tower, known as the Beekman Residences, designed by Gerner Kronick + Valcarcel Architects.
The Temple Court Building’s atrium was designated as an interior landmark by the New York City Landmarks Preservation Commission in 2024, recognizing its historical and architectural significance.
