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| Title | Artist | Medium & Support | Creation Date |
| Near Aurora, Illinois | Waugh, Henry W. | ink on paper | mid 19th century |
| Near Oswego, Illinois | Waugh, Henry W. | ink on paper | mid 19th century |
| Scrub Oak, Chrystal Lake, Illinois | Waugh, Henry W. | ink on paper | mid 19th century |
| Devonshire Coast | Richards, William Trost | pencil and ink on paper | 19th century |
| Seascape Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Seascape Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Mountain Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Landscape Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Seascape Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Seascape Study | Richards, William Trost | pencil and ink on paper | 19th century |
| Seascape Scenes | Richards, William Trost | pencil and ink on paper | 19th century |
| Miss M. U. | Richards, William Trost | pencil and ink on paper | 19th century |
| Marine Scene | Richards, William Trost | wash on paper | 19th century |
| Marine Scene | Richards, William Trost | wash on paper | 19th century |
| Untitled | Richards, William Trost | ink wash on paper | 19th century - 20th century |
| Seated Woman | Richards, William Trost | pencil and ink on paper | 19th century |
| The Old Church at Iniskea | Richards, William Trost | pencil and ink on paper | 19th century |
| Portrait | crayon and chalk | 19th century | |
| Portrait of a Woman | chalk/charcoal on canvas | 19th century | |
| Portrait of a Man | chalk/charcoal on canvas | 19th century | |
| Man Proposes | Herford, Oliver | pen and ink | late 19th century - early 20th century |
| Woman with Bonnet | pencil, watercolor, and ink on paper | 19th century | |
| Double Portrait: Man and Woman | watercolor, ink, and pencil on paper | ca. 1830 - 1840 | |
| Profile of Man and Woman | Bascom, Ruth Henshaw | pencil on paper | ca. 1840 |
| The Lynk Homestead, Leesville, N.Y., December 22, 1894 | Vogt, Fritz G. | colored and graphite pencil on paper | December 22, 1894 |