Series I includes two self-portraits that Chapman gave to the Historical Society in 1953. They are arranged in chronological order. The first was taken in 1913 in Chapman's workshop on Bank Street in Greenwich Village. It shows Chapman as a young man working with photographic equipment. The second, taken in 1953, shows a much older Chapman standing in the swamp of a nature preserve in the Palisades, once again posed with camera equipment. Both portraits clearly show his deep interest in photography.

Series II contains twenty photographs taken in downtown New York from 1911 to 1922. Photographs are arranged alphabetically by title. There are many river scenes, often with a bridge in the background as in "East River, Barges, Ferryboat and the Williamsburg Bridge" (1913), "From Fulton Ferry Slip" (1916), "Under Brooklyn Bridge, From Under The Pier on the Brooklyn Side" (1916), and "Boat Basin at The Battery" (1913). "From Brooklyn Bridge" (1916) is taken from beneath the structure of the bridge; this interest in the dynamics of buildings is characteristic of many of Chapman's downtown photographs, and is also reflected in "Woolworth Building from Washington Market" (1915).

Another of Chapman's concentrations was building construction. Downtown New York was constantly changing as it is today, and Chapman showed this clearly in his photographs. There are two images titled "Construction Work, Wall and William Streets" (1922) which document busy construction sites. Chapman emphasized the shape of the cranes and heavy equipment used, and captured steam escaping from a vent in the background. "The Burling Slip Plant of the New York Steam Corporation Under Construction" (1916) is another photograph which reflects the changing face of downtown New York.

The El train is featured strongly in Chapman's work, perhaps because he rode it daily. "Greenwich Avenue From Sixth Avenue El Station" (1914), "From Chatham Square Station of Third Avenue El" (1915), and "Hanover Square, El Structure Now (1951) to be Demolished" all show the El train, usually taken from below and looking up at the structure of the track.

Series III holds seventeen photographs taken by Chapman from 1913 to 1916. As an inhabitant of the Village and an advocate of photographing one's everyday scenes, Chapman used his own street, Patchin Place, as a subject, and made other pictures of buildings, places of interest, and residential areas often overlooked because of their normalcy. His framing is often close and intimate. Several of the photographs in this series are of alleys where women hung washing; "Minetta Place" (1914), "Clinton Court" (1915), and four photographs entitled, "Grove Court" (1913-1915) each have washing lines as a focal point. "Milligan Place" (1913), another of his intimate courtyard scenes, was photographed in the daytime with a baby carriage in the foreground, and then again at night in "Milligan Place, Night" (1913). This contrasting is used again with "Patchin Place" (1914) and "Patchin Place, Winter" (1915); the first is of that small alley with children playing, and the second is the same alley with snow on the ground.

Another characteristic of this series is Chapman's use of shadow to create visual interest. Two good examples are "Kelly's Alley" (1915), which is a rooftop scene with dramatic use of shadow, and "9½ Jane Street" (1915). In "Washington Arch" (1915) and "Washington Square" (1915), Chapman used a less intimate view. These images are more sweeping and use Washington Arch as the focal point but include buildings in the background. "Fifth Avenue, looking South from Thirteenth Street"(1916), is also a sweeping view of a snowy and busy city street. "'Diagonals' Christopher Street, from Sixth Avenue El Station" (1915) is perhaps Chapman's best-known image, and was shown at more exhibitions than any other of his photographs. In that picture, the view along Christopher Street is framed by the handrails of the El station stairs, giving it an angular feel.

Series IV consists of twenty-one photographs. Many images feature the water, including "Boat Basin, Harlem Ship Canal" (1913) and "Harlem River, From the Washington Bridge at One Hundred and Eighty First Street, looking South" (1909). Chapman also took two photographs of Admiral Peary's ship, "The Roosevelt", in 1908, one at close range with a policeman in the foreground looking at her. A second photograph shows a scene of excitement as "The Roosevelt" embarks for the North Pole; the ship is shown alongside others that were perhaps giving her a send-off.

Madison Square is the focus of several photographs. Three entitled "Madison Square" show the Square in summer and again in winter with snow on the ground; two were taken in 1913 and the third in 1912. "Madison Square from Twenty Sixth Street" (1910) again shows the Square in winter with snow-covered trees creating a sharp contrast to the angular Flatiron building in the background. "Madison Square, Looking Out From Under the Colonnade of Madison Square Garden" (1913) is another of Chapman's photographs of Madison Square, taken from an interesting angle below a colonnade which overhangs and frames the square with the statue of Stanford White in the center. "Metropolitan Tower, Looking East Across Madison Square. The "Parkhurst" Church in the Background" (1914) employs both shadow and framing. The photograph has two tall buildings that are completely in shade. Between them is the Metropolitan Tower bathed in sunlight, with snow piled up on the sides of the street, and people hurrying past.

In "From Recreation Pier, 24th Street and East River" (1912) and "From a West Shore Railroad Ferryboat" (1916), Chapman's framing is exquisite. The first has a ship viewed through a doorway, a simple but effective composition. The second is of the cityscape, framed by men lounging casually. In "Boat Basin, Spuyten Duyvil" (1913), Chapman uses the same framing technique, but employing the branches of a tree.

Chapman's interest in construction is again seen in two 1916 photographs, "The 'Derrick' Close-up, Excavation on Madison Avenue," and "'The Derrick' Going Down, Excavation on Madison Avenue." Both show heavy equipment, men working and plenty of steam, with a particular focus on the equipment. "Excavation, 7th Avenue and 24th Street" (1912) is another photograph which shows construction, and the changing face of the city.

Dramatic use of shadow is once again evident in this series in "Madison Avenue, Looking North From 38th Street" (1916). Chapman focuses on a row of brownstone houses with a large building rising behind; one side of the street is in complete shade, but the brownstones and building behind are in bright sunlight.