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Hop On a Citi Bike and Visit 26 Historic Downtown Buildings

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Whether you like it or not, Citi Bike launches on Memorial Day, bringing 5,500 new blue bikes to the streets of New York. The 300 docking stations scattered throughout Lower Manhattan and parts of Brooklyn create a bike share that's meant for leisurely, hop on, hop off rides around town, so what better way to test out the system than with an architectural tour? Downtown holds many of Manhattan's iconic skyscrapers, but for this tour, we chose 26 under-the-radar gems, all of which are more than 100 years old and located south of 14th Street. Our map doesn't include Citi Bike stations, but if you're worried about locating them, there's an app for that.

· Citi Bike coverage [Curbed]
· Citi Bike [official]

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1. Northern Dispensary

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165 Waverly Place
New York, NY 10014

1827. This Georgian triangular structure is the only building in New York, or perhaps anywhere, with one side on two streets (Grove and Christopher) and two sides on one street (Waverly Place). Edgar Allen Poe was once treated here.

2. The Lockwood DeForest House

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7 East 10th Street
New York, NY 10003

Van Campen Taylor, 1887. Teak-encrusted townhouse built by a teak manufacturer. On one of the most picturesque residential blocks in Greenwich Village. Next door to home of Village writer Dawn Powell. In 1900 a writer for House Beautiful called it the “most beautiful Indian House in America."

3. 128 East 13th Street

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128 East 13th Street
New York, NY 10003

Jardine, Kent, and Jardine, 1903. New York's last surviving horse and carriage auction mart building, used as an assembly line training facility for women during WWII, and later used as a studio by artist Frank Stella for several decades. Saved from destruction by the Greenwich Village Society for Historic Preservation in 2006.

4. Webster Hall

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125 E 11th St
New York, NY 10003
(212) 353-1600
Visit Website

Charles Rentz, 1886. Three-story ballroom and concert hall, made of Philadelphia Brick with stone accents and unglazed red terra-cotta. Adorned with fluted bracketed cornice and decorative terra-cotta panels.

5. The Cooper Union

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41 Cooper Sq
New York, NY 10003
(212) 353-4000
Visit Website

Frederick A. Peterson, 1859. The muscular neo-Romanesque shell of Cooper Union is the oldest standing steel framed building in America. Peter Cooper envisioned the elevator as the interior transportation of the future and installed a cylindrical shaft in Cooper Union (before the elevator was actually invented!). But for more than 100 years a box-shaped cab ran in Cooper's shaft, a square peg in a round hole.

6. Judson Memorial Church

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55 Washington Sq S
New York, NY 10012

McKim, Mead, and White, 1892. Baptist Pastor Edward Judson began a campaign in the late 19th century to build "the most beautiful churches among the homes of the poor, so that it would be only a step from the squalor of the tenement houses." John D. Rockefeller Sr. donated the money for the church to be built and Judson named it after his father, a Protestant missionary. Architectural firm Stanford, Mead, and White described their design as, "Romanesque, strongly influenced by early basilica." John La Farge designed stained glass windows which are still in the church.

7. Narrowest House In New York

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75 1/2 Bedford St
New York, NY 10014

1873. Both writer Edna St. Vincent Millay and anthropologist Margaret Mead lived here. It's less than 10 feet wide on the exterior.

8. The Archive

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666 Greenwich St
New York, NY 10014
(212) 691-9800
Visit Website

Willoughby J. Edbrooke, William Martin Aiken, James Knox, 1899. Completely out of scale with the West Village of today, the red brick archival building's great arches and massive piers at street level "show the heavy masonry required to support tall buildings before the steel skeleton came into general use."

9. Bayard-Condict Building

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67 Bleecker Street
New York, NY 10012

Louis Sullivan, 1898. The only New York building by Louis Sullivan, father of the skyscraper. Vertical! Steel! Organic bas relief on the facade!

10. Russian Orthodox Cathedral of the Holy Virgin Protection

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59 E 2nd St
New York, NY 10003
(212) 677-4664

1891. This stunner of a church was built in the Gothic Revival style by architect J.C. Cady (the same guy who designed the American Museum of Natural History’s south addition). The facade is made from Kentucky limestone, and it has beautifully carved stained glass windows.

11. Little Singer Building

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561 Broadway
New York, NY 10012

1903. A Soho classic, the Little Singer Building was restored to its original grandeur in 2008. Architect Ernest Flagg created the whimsical, delicate design with lace-like cast and wrought iron ornamentation, red brick and terracotta detailing, and large expanses of windows. The facade is topped with an elaborate iron arch and ornate cornice supported by scrolled iron brackets. Flagg was inspired by Parisian architecture, and the exposed iron and steel look was very avant-garde for the time. [Photo via Curbed Flickr pool]

12. 256 Mott Street

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256 Mott Street
New York, NY 10012

1888-89. John Jacob Astor III provided funds for this Victorian Gothic building to be constructed for the Children's Aid Society. It was designed by Vaux & Radford (the same Vaux of the park-designing duo Olmsted and Vax) with red Pennsylvania bricks and a brownstone and terracotta trim. It cost Astor a whopping $42,000. Today, the building is residential. [Photo]

13. Haughwout Building

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1857. The Haughwout Building is a great example of Soho's many cast iron buildings. Architect John P. Gaynor created the design using cast-iron from Daniel D. Badger's Architectural Iron Works. Although the design was typical of the time, the dual street fronts made the building a challenge—the weight of the two facades could bring down the building. According to Wikipedia, "To avoid this, rather than hanging the facades off the brickwork, as was usually done, Gaynor and Badger convinced Haughwout to allow them to use the strength of the cast-iron itself to support the building. This use of a structural metal frame was a precursor to the steel-framed skyscrapers that would start to be built in the early 20th century; in fact, some consider it to the first skyscraper and 'the most important cast-iron structure ever built.'"

14. Angel Orensanz Foundation

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172 Norfolk St
New York, NY 10002

1849. This Gothic Revival synagogue is no longer used as a religious institution, but its beautiful architecture makes it a popular place for weddings. The building was original constructed by Alexander Saeltzer for the Reform Congregation Ansche Chesed. At the time, it was the largest synagogue built in the United States, and it is still one of the few designed in the Gothic Revival style. It was purchased by artist Angel Orensanz in the '80s and lovingly restored.

15. The Police Building

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240 Centre St
New York, NY 10013

1905-1909. A Curbed favorite, the grand Police Building was designed and built by the firm of Hoppin & Koen to replace the older police headquarters on Mulberry Street. The majestic Beaux Arts masterpiece was designed to "to impress both the officer and the prisoner with the majesty of the law." The dome and facade are filled with intricate carved details, like the graceful female figures that hold placards with the name of each borough. In the '80s, the building was converted to condos, and many, like the Gwathmey-designed gymnasium home, are some of the most unique spaces in the city.

16. Henry Street Settlement

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265 Henry St
New York, NY 10002

circa 1827. The three Federal Style rowhouses that make up the Henry Street Settlement were built on streets laid out on Henry Rutgers' farmland. While they look similar, the three buildings have a few distinctions from one another, like the type of cornice and the styling of the lintels. You can read a detailed history of the architecture and the alterations that have been made on the Settlement's website.

17. The Forward Building

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175 East Broadway
New York, NY 10002

1912. Like many other buildings on this map, the old Jewish Forward Building is now residential. Architect George Boehm created the building as offices for the Forward newspaper, embellishing the facade with marble columns, stained glass windows, and carved base reliefs depicting prominent Socialist figures, including Karl Marx. [Photo by Joel Raskin/Curbed Flickr pool]

18. Jarmulowsky Bank Building

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54 Canal Street
New York, NY 10002

1912. This 12-story Beaux Arts beauty has been in the news lately because the owner recently won Landmarks approval to restore the historic structure and convert it into a hotel. The renovation will gussy up the limestone and terracotta facade created by architects Rouse & Goldstone, but unfortunately, it will not bring back the building's original cupola. [Photo via the LoDown]

19. American Thread Building

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260 West Broadway
New York, NY 10013

1896. Curbed recently dove into the history of the William B. Tubby-design American Thread Building, as it encapsulates Tribeca's role as a manufacturing center in the early 20th century. Author Lisa Santoro wrote: "Completed in 1896, the eleven-story Renaissance revival building conformed to the street, creating a stately façade that curved nearly 175 feet from Beach Street along the building's south façade onto West Broadway. The building's three-story base, comprised of an alternating limestone and Roman brick pattern, was to house the Wool Exchange. [...] The building features various decorative elements that distinguish it from the factories and warehouses prevalent in the area; such features include round arched windows, scrolled iron cartouche spandrel panels, keystones, medallions and Roman Ionic columns around the entranceway." Today, the building holds condos (one of which is an impressive domed penthouse).

20. Ahrens Building

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70 Lafayette Street
New York, NY 10013

1894-95. Located in the city's Civic Center among the courthouses and high rises, the Ahrens Building by George H. Griebel is an overlooked Romanesque Revival gem. The facade along Lafayette Street has lovely details that blend sculpted terracotta and brick to create a red and white pattern within the arched windows. The limestone base is ornately carved around the entranceway, and three long arches frame bays filled with metal-clad oriel windows. [Photo]

21. The Mohawk Atelier

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161 Duane St
New York, Ny 10013

1891. Built for a confectioner but best know as the former home of the Mohawk Electric Company, the Romanesque Revival building at 161 Duane Street underwent an extensive restoration in 2007 as part of its conversion into condos. The sandstone and brick facade is dominated by broad arches that frame the windows. It's topped with a carved balustrade and cornice with a small turret at the corner, and the bottom is punctuated by a rusticated design of protruding bands.

22. 5 Beekman Street

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5 Beekman Street
New York, NY

This landmark is being transformed into 285 hotel rooms and 85 residential units. The landmark status means that, thankfully, the building's lovely Victorian atrium will be preserved in the conversion.

23. St. Paul's Chapel

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209 Broadway
New York, NY 10006
(212) 602-0874
Visit Website

1764. The older, smaller sister to the famed Trinity Church, St. Paul's Chapel is one of the oldest structures in New York City. Constructed by Thomas McBean, the Georgian-style chapel is made of Manhattan mica-schist with brownstone quoins and the classic boxy portico.

24. Corbin Building

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192 Broadway
New York, NY 10038

1888. For years, the Corbin Building was covered with black grime, hiding its true beauty, but a comprehensive overhaul by the MTA (thank you, Fulton Center!) recently restore its brick, stone, and terracotta facade. The exterior features meticulously carved ornamentation, while the interiors boast their own intricacies, like sculpted wooden window frames and tile ceilings.

25. Delmonico's

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2 South William Street
New York, NY 10005

1891. Designed by James Brown Lord, this brick building is more famous for the restaurant, the iconic Delmonico's steakhouse, it holds than its architecture. The building is a classic Romanesque Revival structure that was praised by the Times for being "admirable in its simplicity and elegance." It was landmarked in 1995, and the commission described it as such: "Faced in orange iron-spot brick, brownstone, andterracotta, the facade features giant arcades and a rounded corner bay which is distinguished by two tiers of giant columns and a semicircular entrance porch. The sensitive handling of materials, rich colors, and elaborate decorative programincorporating Renaissance motifs makes this one of the finest surviving late-nineteenth-century buildings in Manhattan's financial district."

26. Fraunces Tavern

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54 Pearl St.
New York, NY 10004

1719. The Fraunces Tavern is famous for its prominent role in the Revolutionary War (George Washington dined here), but it's also architecturally important because it's one of the oldest buildings in the city. It was originally built by Etienne Delancey as a family residence.

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1. Northern Dispensary

165 Waverly Place, New York, NY 10014

1827. This Georgian triangular structure is the only building in New York, or perhaps anywhere, with one side on two streets (Grove and Christopher) and two sides on one street (Waverly Place). Edgar Allen Poe was once treated here.

165 Waverly Place
New York, NY 10014

2. The Lockwood DeForest House

7 East 10th Street, New York, NY 10003

Van Campen Taylor, 1887. Teak-encrusted townhouse built by a teak manufacturer. On one of the most picturesque residential blocks in Greenwich Village. Next door to home of Village writer Dawn Powell. In 1900 a writer for House Beautiful called it the “most beautiful Indian House in America."

7 East 10th Street
New York, NY 10003

3. 128 East 13th Street

128 East 13th Street, New York, NY 10003

Jardine, Kent, and Jardine, 1903. New York's last surviving horse and carriage auction mart building, used as an assembly line training facility for women during WWII, and later used as a studio by artist Frank Stella for several decades. Saved from destruction by the Greenwich Village Society for Historic Preservation in 2006.

128 East 13th Street
New York, NY 10003

4. Webster Hall

125 E 11th St, New York, NY 10003

Charles Rentz, 1886. Three-story ballroom and concert hall, made of Philadelphia Brick with stone accents and unglazed red terra-cotta. Adorned with fluted bracketed cornice and decorative terra-cotta panels.

125 E 11th St
New York, NY 10003

5. The Cooper Union

41 Cooper Sq, New York, NY 10003

Frederick A. Peterson, 1859. The muscular neo-Romanesque shell of Cooper Union is the oldest standing steel framed building in America. Peter Cooper envisioned the elevator as the interior transportation of the future and installed a cylindrical shaft in Cooper Union (before the elevator was actually invented!). But for more than 100 years a box-shaped cab ran in Cooper's shaft, a square peg in a round hole.

41 Cooper Sq
New York, NY 10003

6. Judson Memorial Church

55 Washington Sq S, New York, NY 10012

McKim, Mead, and White, 1892. Baptist Pastor Edward Judson began a campaign in the late 19th century to build "the most beautiful churches among the homes of the poor, so that it would be only a step from the squalor of the tenement houses." John D. Rockefeller Sr. donated the money for the church to be built and Judson named it after his father, a Protestant missionary. Architectural firm Stanford, Mead, and White described their design as, "Romanesque, strongly influenced by early basilica." John La Farge designed stained glass windows which are still in the church.

55 Washington Sq S
New York, NY 10012

7. Narrowest House In New York

75 1/2 Bedford St, New York, NY 10014

1873. Both writer Edna St. Vincent Millay and anthropologist Margaret Mead lived here. It's less than 10 feet wide on the exterior.

75 1/2 Bedford St
New York, NY 10014

8. The Archive

666 Greenwich St, New York, NY 10014

Willoughby J. Edbrooke, William Martin Aiken, James Knox, 1899. Completely out of scale with the West Village of today, the red brick archival building's great arches and massive piers at street level "show the heavy masonry required to support tall buildings before the steel skeleton came into general use."

666 Greenwich St
New York, NY 10014

9. Bayard-Condict Building

67 Bleecker Street, New York, NY 10012

Louis Sullivan, 1898. The only New York building by Louis Sullivan, father of the skyscraper. Vertical! Steel! Organic bas relief on the facade!

67 Bleecker Street
New York, NY 10012

10. Russian Orthodox Cathedral of the Holy Virgin Protection

59 E 2nd St, New York, NY 10003

1891. This stunner of a church was built in the Gothic Revival style by architect J.C. Cady (the same guy who designed the American Museum of Natural History’s south addition). The facade is made from Kentucky limestone, and it has beautifully carved stained glass windows.

59 E 2nd St
New York, NY 10003

11. Little Singer Building

561 Broadway, New York, NY 10012

1903. A Soho classic, the Little Singer Building was restored to its original grandeur in 2008. Architect Ernest Flagg created the whimsical, delicate design with lace-like cast and wrought iron ornamentation, red brick and terracotta detailing, and large expanses of windows. The facade is topped with an elaborate iron arch and ornate cornice supported by scrolled iron brackets. Flagg was inspired by Parisian architecture, and the exposed iron and steel look was very avant-garde for the time. [Photo via Curbed Flickr pool]

561 Broadway
New York, NY 10012

12. 256 Mott Street

256 Mott Street, New York, NY 10012

1888-89. John Jacob Astor III provided funds for this Victorian Gothic building to be constructed for the Children's Aid Society. It was designed by Vaux & Radford (the same Vaux of the park-designing duo Olmsted and Vax) with red Pennsylvania bricks and a brownstone and terracotta trim. It cost Astor a whopping $42,000. Today, the building is residential. [Photo]

256 Mott Street
New York, NY 10012

13. Haughwout Building

New York, NY 10012

1857. The Haughwout Building is a great example of Soho's many cast iron buildings. Architect John P. Gaynor created the design using cast-iron from Daniel D. Badger's Architectural Iron Works. Although the design was typical of the time, the dual street fronts made the building a challenge—the weight of the two facades could bring down the building. According to Wikipedia, "To avoid this, rather than hanging the facades off the brickwork, as was usually done, Gaynor and Badger convinced Haughwout to allow them to use the strength of the cast-iron itself to support the building. This use of a structural metal frame was a precursor to the steel-framed skyscrapers that would start to be built in the early 20th century; in fact, some consider it to the first skyscraper and 'the most important cast-iron structure ever built.'"

14. Angel Orensanz Foundation

172 Norfolk St, New York, NY 10002

1849. This Gothic Revival synagogue is no longer used as a religious institution, but its beautiful architecture makes it a popular place for weddings. The building was original constructed by Alexander Saeltzer for the Reform Congregation Ansche Chesed. At the time, it was the largest synagogue built in the United States, and it is still one of the few designed in the Gothic Revival style. It was purchased by artist Angel Orensanz in the '80s and lovingly restored.

172 Norfolk St
New York, NY 10002

15. The Police Building

240 Centre St, New York, NY 10013

1905-1909. A Curbed favorite, the grand Police Building was designed and built by the firm of Hoppin & Koen to replace the older police headquarters on Mulberry Street. The majestic Beaux Arts masterpiece was designed to "to impress both the officer and the prisoner with the majesty of the law." The dome and facade are filled with intricate carved details, like the graceful female figures that hold placards with the name of each borough. In the '80s, the building was converted to condos, and many, like the Gwathmey-designed gymnasium home, are some of the most unique spaces in the city.

240 Centre St
New York, NY 10013

16. Henry Street Settlement

265 Henry St, New York, NY 10002

circa 1827. The three Federal Style rowhouses that make up the Henry Street Settlement were built on streets laid out on Henry Rutgers' farmland. While they look similar, the three buildings have a few distinctions from one another, like the type of cornice and the styling of the lintels. You can read a detailed history of the architecture and the alterations that have been made on the Settlement's website.

265 Henry St
New York, NY 10002

17. The Forward Building

175 East Broadway, New York, NY 10002

1912. Like many other buildings on this map, the old Jewish Forward Building is now residential. Architect George Boehm created the building as offices for the Forward newspaper, embellishing the facade with marble columns, stained glass windows, and carved base reliefs depicting prominent Socialist figures, including Karl Marx. [Photo by Joel Raskin/Curbed Flickr pool]

175 East Broadway
New York, NY 10002

18. Jarmulowsky Bank Building

54 Canal Street, New York, NY 10002

1912. This 12-story Beaux Arts beauty has been in the news lately because the owner recently won Landmarks approval to restore the historic structure and convert it into a hotel. The renovation will gussy up the limestone and terracotta facade created by architects Rouse & Goldstone, but unfortunately, it will not bring back the building's original cupola. [Photo via the LoDown]

54 Canal Street
New York, NY 10002

19. American Thread Building

260 West Broadway, New York, NY 10013

1896. Curbed recently dove into the history of the William B. Tubby-design American Thread Building, as it encapsulates Tribeca's role as a manufacturing center in the early 20th century. Author Lisa Santoro wrote: "Completed in 1896, the eleven-story Renaissance revival building conformed to the street, creating a stately façade that curved nearly 175 feet from Beach Street along the building's south façade onto West Broadway. The building's three-story base, comprised of an alternating limestone and Roman brick pattern, was to house the Wool Exchange. [...] The building features various decorative elements that distinguish it from the factories and warehouses prevalent in the area; such features include round arched windows, scrolled iron cartouche spandrel panels, keystones, medallions and Roman Ionic columns around the entranceway." Today, the building holds condos (one of which is an impressive domed penthouse).

260 West Broadway
New York, NY 10013

20. Ahrens Building

70 Lafayette Street, New York, NY 10013

1894-95. Located in the city's Civic Center among the courthouses and high rises, the Ahrens Building by George H. Griebel is an overlooked Romanesque Revival gem. The facade along Lafayette Street has lovely details that blend sculpted terracotta and brick to create a red and white pattern within the arched windows. The limestone base is ornately carved around the entranceway, and three long arches frame bays filled with metal-clad oriel windows. [Photo]

70 Lafayette Street
New York, NY 10013

21. The Mohawk Atelier

161 Duane St, New York, Ny 10013

1891. Built for a confectioner but best know as the former home of the Mohawk Electric Company, the Romanesque Revival building at 161 Duane Street underwent an extensive restoration in 2007 as part of its conversion into condos. The sandstone and brick facade is dominated by broad arches that frame the windows. It's topped with a carved balustrade and cornice with a small turret at the corner, and the bottom is punctuated by a rusticated design of protruding bands.

161 Duane St
New York, Ny 10013

22. 5 Beekman Street

5 Beekman Street, New York, NY

This landmark is being transformed into 285 hotel rooms and 85 residential units. The landmark status means that, thankfully, the building's lovely Victorian atrium will be preserved in the conversion.

5 Beekman Street
New York, NY

23. St. Paul's Chapel

209 Broadway, New York, NY 10006

1764. The older, smaller sister to the famed Trinity Church, St. Paul's Chapel is one of the oldest structures in New York City. Constructed by Thomas McBean, the Georgian-style chapel is made of Manhattan mica-schist with brownstone quoins and the classic boxy portico.

209 Broadway
New York, NY 10006

24. Corbin Building

192 Broadway, New York, NY 10038

1888. For years, the Corbin Building was covered with black grime, hiding its true beauty, but a comprehensive overhaul by the MTA (thank you, Fulton Center!) recently restore its brick, stone, and terracotta facade. The exterior features meticulously carved ornamentation, while the interiors boast their own intricacies, like sculpted wooden window frames and tile ceilings.

192 Broadway
New York, NY 10038

25. Delmonico's

2 South William Street, New York, NY 10005

1891. Designed by James Brown Lord, this brick building is more famous for the restaurant, the iconic Delmonico's steakhouse, it holds than its architecture. The building is a classic Romanesque Revival structure that was praised by the Times for being "admirable in its simplicity and elegance." It was landmarked in 1995, and the commission described it as such: "Faced in orange iron-spot brick, brownstone, andterracotta, the facade features giant arcades and a rounded corner bay which is distinguished by two tiers of giant columns and a semicircular entrance porch. The sensitive handling of materials, rich colors, and elaborate decorative programincorporating Renaissance motifs makes this one of the finest surviving late-nineteenth-century buildings in Manhattan's financial district."

2 South William Street
New York, NY 10005

26. Fraunces Tavern

54 Pearl St., New York, NY 10004

1719. The Fraunces Tavern is famous for its prominent role in the Revolutionary War (George Washington dined here), but it's also architecturally important because it's one of the oldest buildings in the city. It was originally built by Etienne Delancey as a family residence.

54 Pearl St.
New York, NY 10004