| Years | Image | Event | Description | Keywords |
| 1805 | | Rock outcropping in Franconia Notch first noticed by road workers. | | Old Man, profile |
| 1830 | | Theodore Dwight, The Northern Traveller (guidbook) mentions "Old Man of the Mountains." | | old man, profile |
| 1848 | | William Oakes, Scenery of the White Mountains | Oakes said that from one angle the profile resembled a "toothless old woman in a mob cap." From the best angle, however, it showed a man with character "fixed and firm." | old man, profile |
| 1850 | | Nathaniel Hawthorne, "The Great Stone Face" | | old man, profile" mountain |
| 1856 | | Benjamin Willey, Incidents in White Mountain History | Earliest published version of a comment later attributed to Daniel Webster. ""Men put out signs representing their different trades; jewellers hang out a monster watch; shoemakers, a huge boot; and, up in Franconia, God Almighty has hung out a sign that in New England he makes men." | profile, old man |
| 1930 | | Old Man of the Mountain promoted as a tourist attraction. | In the late 1920s the State of New Hampshire began efforts to stabilize the crumbling formation. | profile |
| 2003 | | Old Man of the Mountains collapses | | profile |