| 1850 | Date which Cliff House promotional literature claims that it was first opened.
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| 1863 | Actual date of Cliff House opening. |
| 1865 | Aerialist James Cook walks a wire from the Cliff House terrace to Seal Rocks and back again.
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| 1881 | Adolph Sutro buys the Cliff House. |
| 1884 | Swimmer D.F. Riehl braves the cold waters of Land's End to swim from Cliff House to Seal Rocks and back. |
| 1887 | The U.S. Congress gives Seal Rocks to the City and County of San Francisco for protection. |
| 1888 | Construction of Land's End Scenic Railroad. |
| 1894 | First Cliff House burns down on Christmas Eve. |
| 1896 | Sutro Baths open. |
| 1896 | Adolph Sutro rebuilds the Cliff House in the style of a classic French chateau complete with an observation tower. |
| 1898 | Death of Adolph Sutro. |
| 1899 | The Cliff House receives the first ship-to-shore wireless transmission in the U.S. from the San Francisco lightship. |
| 1899 | Robert F. Morrow buys the Sutro Railroad for $215,000. |
| 1902 | Sutro Baths damaged by heavy seas. |
| 1906 | The Great Earthquake fails to dislodge the resort from its perch. |
| 1907 | Second Cliff House burns down! |
| 1909 | Third Cliff House opens. |
| 1916 | Playland-by-the-Sea Merry-Go-Round opens. |
| 1922 | Playland-by-the-Sea Big Dipper roller coaster opens. |
| 1923 | Funhouse at Playland-by-the-Sea opens. |
| 1952 | George Whitney acquires Cliff House from the Sutro Family. |
| 1955 | Sky-Tram from Cliff House to Point Lobos opens. |
| 1955 | Playland's "Big Dipper" is demolished. |
| 1966 | Sutro Baths burn down. |
| 1972 | Playland-by-the-Sea closes. |
| 1977 | National Park Service acquires Cliff House for use as a Visitor's Center in the Golden Gate National Recreation Area. |
| 1989 | The Quake of '89 fails to propel the Cliff House into the sea. |