The H.M. Chester Photograph Collection consists of glass negatives, measuring 4 x 5 to 6 ½ x 8 ½ inches, depicting prominent residences, tourist attractions, railroads, fairs, and natural landscapes across the United States, but especially in California, Colorado, Michigan, New York, Washington, and at Yellowstone National Park. The collection spans the period from 1892-1910; most of the negatives are undated but were probably created close to this time period. The collection is arranged alphabetically by state and thereunder by city or other geographical feature; views of the Pan-American Exposition in Buffalo have been filed under Niagara Falls/Buffalo because the majority of the photographs relate to Niagara Falls. Images of Yellowstone National Park have been filed under Wyoming. Views of Mexico are filed at the end of the states. Views of unidentified locations have been filed in a miscellaneous subseries at the end of the collection; they are organized by subject. One box of oversized negatives has been filed at the end of the collection; it also contains the photographic prints. It is unclear whether the photographs in this collection were taken by H.M. Chester or by another member of his traveling party. Some numbers have been subdivided by letter due to the addition of discovered negatives after the collection was processed.

The collection includes views of the Alaska-Yukon-Pacific Exposition held in Seattle in 1909, the Lewis and Clark Centennial Exposition held in Portland, Oregon in 1905, and the Pan-American Exposition held in 1901 in Buffalo (and associated hydroelectric projects at Niagara Falls). The collection includes photographs of H.M. Chester, his wife, and their fellow travelers at many of the featured locations. California is the most heavily represented state in the collection. A series of Yosemite National Park and Mount Tamalpais landscape photographs are complemented by more urban photographs taken in Los Angeles and at San Francisco and Oakland landmarks. In New York, Rochester and Niagara Falls are the most heavily represented areas, although some images of New York City buildings and events such as the Dewey Celebration and the Grant's Tomb Dedication Parade are included.

Foreign views on the Canadian side of Niagara Falls and of the Mexican border, probably near Tijuana, are also present. The Connecticut negatives, of which several are oversized, consist primarily of images of a farm in North Stonington, Connecticut (which is probably the Chester family farm) as well as photographs of H.M. Chester and his wife.

The miscellaneous subseries includes photographs of individuals, animals, unidentified landscapes, ships, streetscapes, and two 1907 flower shows. A few portraits of a man identified as W.E. McCarthy are also present.