| 1858 | — | Theodore Roosevelt is born on October 27 in New York City |
| 1880 | — | He graduates from Harvard with high honors, then marries Alice Lee on October 27 |
| 1881 | — | Roosevelt wins election to the New York State Assembly |
| 1884 | — | On February 12, Roosevelt’s first child, Alice Lee, is born; on February 14, both Roosevelt’s wife, Alice, and his mother die |
| 1886 | — | Roosevelt marries Edith Carow on December 2 |
| 1887 | — | Roosevelt and Edith’s first child, Theodore Jr., is born on September 13 |
| 1889 | — | Roosevelt begins working for the US Civil Service Commission; his son Kermit is born on October 10 |
| 1891 | — | The Roosevelts have a daughter, Ethel, on August 13 |
| 1894 | — | Archibald, Roosevelt’s third son, is born on April 10 |
| 1895 | — | Roosevelt returns to New York City to serve on the Board of Police Commissioners |
| 1897 | — | President William McKinley names Roosevelt the assistant secretary of the Navy; on November 19 the Roosevelts’ last child, Quentin, is born |
| 1898 | — | Roosevelt is elected governor of New York |
| 1900 | — | Running with President William McKinley, Roosevelt is elected vice president |
| 1901 | — | President McKinley is shot and subsequently dies, and Roosevelt becomes president on September 14 |
| 1904 | — | Roosevelt wins election as president |
| 1918 | — | Roosevelt’s son Quentin is killed while fighting in France |
| 1919 | — | Theodore Roosevelt dies on January 6 in Oyster Bay, New York |