This series chiefly contains correspondence comprised of loose letters, letter books, and letter copy books. The correspondence spans the entire period covered by the series, and involves Dutcher in his numerous political and business capacities, including Supervisor of the Internal Revenue, Pension Agent for the Eastern District of New York, Appraiser of the Port of New York, New York State Supervisor of Public Works, Director of Metropolitan Life Insurance, President of Union Dime, and President of the Hamilton Trust Company. Additional letters illuminate Dutcher's active role in the Republican Party and his involvement in numerous state and local professional, political, and civic member organizations. The series also includes documents and reports related to certain issues overseen by Dutcher as Supervisor of Public Works, including a legal dispute between the West Shore & Buffalo Railroad Company and the Oxford Copper and Sulphur Company, in which Dutcher was arbitrator, and an application from the West Shore & Buffalo Railroad Company to construct its road over canal lands in Montgomery County. Additional items include financial records, and handwritten and typed transcripts of speeches delivered or received by Dutcher at various events hosted by professional, political, and civic organizations.

This series contains a small amount of correspondence relating to certain members of the Dutcher family, and materials relating to Silas B. Dutcher's death in 1909. The correspondence mostly concerns Dutcher's daughter, Edith, and the prospect of her taking a clerical position in the United States Pension Office, an arrangement made possible by her father. Edith ultimately rejects the offer, owing to family committments at home, but recommends a cousin for the position. The remainder of the correspondence is between Dutcher's widow, Rebecca, and the National Memorial, in which the Memorial requests to receive a photograph of the recently-deceased Dutcher. Additional items relating to Dutcher's death include condolences sent to the Dutcher family from the State of New York, the Hamilton Trust Company, and other organizations and personal friends; and photocopies of obituaries of Dutcher clipped from various newspapers. Finally, the series also includes a typed biography and genealogy of Dutcher, the author of which is unknown.

This series contains loose newspaper clippings compiled by Silas B. Dutcher and his family throughout the period 1853 to 1909 and relating to a wide range of political and social issues. Certain clippings have been filed together according to their predominant subject matter. These clippings cover such topics as Dutcher's work as Supervisor of Public Works, particularly in regard to the management of New York's canals; Dutcher's private and family lives; trade laws; the New York Customs House; the death of New York Tribune editor Horace Greeley; and the financial scandal involving Tammany Hall's William "Boss" Tweed, among others. All remaining clippings have been grouped together as either miscellaneous or general political clippings. There is also one page clipped from an 1862 French-language newspaper, the contents of which seem to relate to certain events of the American Civil War.

The series also contains several pieces of ephemera relating to Dutcher's involvement in the Republican Party and various other political and civic organizations, including the Brooklyn Masonic Veterans, the Grand Army of the Republic U.S. Grant Post No. 327, and the Department of Parks of the Boroughs of Brooklyn and Queens. These items include announcements for and invitations to banquets and dinners; progams for commemorative ceremonies; circulars relating to Republican candidates in various elections; and the honorary ribbon worn by Dutcher as a Kings County Delegate to the 1904 New York State Republican Convention. Other items seem to relate to Dutcher's personal interest in American history, such as images of Abraham Lincoln and Alexander Hamilton, and handwritten copies of correspondence between Ulysses S. Grant and Robert E. Lee regarding the surrender at Appomattox Court House that ended the Civil War. Additional ephemeral items relate to the Dutcher family and include Sunday school cards and awards for Edith and Malcolm Dutcher; a children's coloring book; and a program for an opera at the Century Opera House.

This series consists of five large scrapbooks containing news clippings and ephemera compiled by Dutcher's wife, Rebecca, and his daughter, Jessie. Two of the scrapbooks contain articles clipped from various New York newspapers and relating to Dutcher's political and business careers, as well as several broad political and business issues. Together, these two scrapbooks offer an exhaustive account of the general political and business climates of the New York City area, New York State, and, to a lesser extent, the United States, from the mid-19th to the early 20th centuries. The remaining three scrapbooks also include articles on Dutcher's careers, but mainly focus on the personal interests of Rebecca and Jessie. These scrapbooks contain clippings of articles on theater, fine arts, literature, fashion, culinary arts, religion, Brooklyn history, and general social and cultural news. Clippings containing obituaries of personal friends, prominent New York citizens, and national celebrities are also included. While the clippings mainly relate to the New York City area, they also contain information on national and international events and issues. A variety of ephemera is also included in these three scrapbooks, including programs for theatrical productions, recitals, and lectures; commencement and excercise programs from various Brooklyn schools, including Girls' High School and Pratt Institute; programs for various community events; marriage invitations and announcements; advertisements; and images of performers and celebrities. One of these latter scrapbooks is housed separately from the rest of the collection in an oversize box.

This series contains honorary certificates and certificates of appointment from several organizations and governmental bodies in which Silas B. Dutcher served in varying capacities. Represented institutions include the Twelfth Street Reformed Church, the Long Island Historical Society (now the Brooklyn Historical Society), the Brooklyn and Long Island Sanitary Fair, the Holland Society of New York, the Brooklyn Masonic Veterans, the American Academy of Political and Social Science, the Kings Park State Hospital, the Society of Old Brooklynites, the Grand Army of the Republic U.S. Grant Post No. 327, the Chamber of Commerce of the State of New York, the Department of Internal Revenue, the Sunday School of Memorial Presbyterian Church, the Mechanics' Savings Bank of Brooklyn, and the Brooklyn Institute of Arts and Sciences. Some of the certificates are housed separately from the rest of the collection in an oversize box. The series also includes one certificate awarded to Edith Dutcher by the City of Brooklyn Department of Public Instruction.