Click main image below to view enlargements and captions.

View, New York City, Upper West Side, Henry Rile, Antique Drawings, 1912-13


Henry E. Rile (1841-1929)
New York City Views, Upper West Side
from New York in the Days Gone By of Old
Black ink, gray wash and graphite on paper
New York: 1912-1913
11 x 14 inches, overall, or smaller, average approximate
$375 each

Bloomingdale Road Near 75th St. in 1863. Formally Major Thompson’s House Later Parrits
Dated Dec. 24, 1912
9 x 12 inches, image
11 x 14 inches, overall

Ex. Mayor Tieman Residence, Broadway 130 St. in 1858
Dated November 30, 1912

Mc-Combs Dam, Harlem River, in 1850. High Bridge.
Dated April 26, 1913
Note: Rebuilt in 1895 and known today as Macombs Dam Bridge.
8.5 x 12.5 inches, image
10.5 x 14 inches, overall

Shanty’s on West Side, 1880
Dated: August 15, 1913
10 x 12.5 inches, overall
Note: Shanties in what was then the rural northwest part of Manhattan.

More Rile Drawings:
Battery & Castle Garden
Brooklyn | Greenwich Village
Lower Manhattan | Midtown
Upper East Side

Henry E. Rile drew this series of views of various places in Manhattan and Brooklyn at the turn of the century. They were issued in a portfolio with a manuscript title page “New York In the Days Gone by of Old…by Henry E. Rile” (full title in description below). Some were drawn on site and others were based on source material including historical prints that had been published in the 19th century in annual New York City Corporation Manuals. Indeed some have the notation by Rile “Manuel [sic]” in the lower margin. Each drawing is titled and dated by Rile, identifying the subject and the date of the image source along with the month, day and year of his drawing. Together, Rile’s drawings record the historic architecture of the City, from famous landmark buildings, churches, and mansions, to simple tenements uptown. He documented commerce and bridges on the East, Hudson, and Harlem Rivers. Portions of Manhattan represented include Uptown, Midtown, the Lower Manhattan financial district, and the area formerly known as Five Points now occupied by the Civic Center and Chinatown. Scarce views of the Upper East Side include a stone mansion known as Smith’s Folly on 61st Street and First Avenue.

Product description continues below.


Drawings of landmark buildings were a specialty of Rile’s. He did at least one other known series of New York City views now in the New-York Historical Society. He also made a series of drawings of places in Whitewater, Wisconsin, where he lived for a number of years as a young man. His drawings exhibit a keen sense of the history of the City and its urban development with the passage of time, from its 17th-century Dutch colonial origins to the early 20th-century, employing attention to accuracy and detail though in simple sketch renderings. The collection as such, as rendered with titles, reflects the deep personal passion that the artist had for the subject matter.

Henry E. Rile was a prolific artist based in New York City who specialized in drawings of buildings in black ink, gray wash and graphite on paper. The New-York Historical Society has a large collection of over 125 works of various views of places in New York City dated between c. 1859 and 1915 by Henry and by his son Lovett Rile (1888-1943), including a sketchbook with 278 drawings. The Whitewater Historical Society has a diary and a collection of pencil drawings and watercolors of buildings in Whitewater, Wisconsin, almost certainly by the same Henry Rile, whom they describe as a “young New York State resident” and “Yankee immigrant who lived in Whitewater between 1856 and 1862.” The drawings were donated to both historical societies by his descendants.

Full manuscript title page: New York In the Days Gone By of Old. Drawings made from Small and Large Pictures From Various Sources Mostly From Corporation Manuals of the City of New York. Some Original. By Henry E. Rile. 1912. [Note: Although Rile evidently created the title page in 1912 many of the drawings were made in later years.]

Condition: Condition varies; please ask for details on specific ones. These are from a uniform series, most titled and dated by the artist. Some of the drawings have images drawn directly on entire sheet; the size of the image varies leaving margins, but generally each image fills the page well. Some of the drawings have images on a separate sheet, mounted to the larger 11 x 14 inch sheet; the size of the image varies leaving margins, but generally each image fills the page well. Some images are vertical; some are horizontal. Some images uniformly toned. Otherwise generally with the usual overall light toning, wear, and handling. Some vary with occasional pale scattered foxing, short tears or minor chips in margins, not obtrusive.


“Henry E. Rile.” New-York Historical Society. 2023. (6 February 2023).

“Lovett Rile.” (6 February 2023).

“March 2008 Newsletter.” Whitewater Historical Society. 2008 March. (6 Feburary 2023).

“Rile Collection.” Whitewater Historical Society. (6 February 2023).

Additional information


20th Century