Collection consists of deeds for property in Portland, Oregon, 1913 and 1924, for Simon Benson; manuscript letter from Simon Benson to his son, Gilbert, November 2, 1920, announcing his marriage; high school certificate of completion from Washington High School, Portland, Oregon, for Gilbert Benson, 1916; Olympia Collegiate Institute diploma for Pamelia Frances Loomis, 1889.

Photographs of the family of Portland businessman Simon Benson and his second wife, Pamelia Loomis, including sons Chester Simon Benson and Gilbert Thereon Benson, and grandchildren Gilbert Thomas Benson and Margaret Benson (later Margaret Maradudin).