| 28 April 1758 | born Westmoreland County, VA son of Spence and Elizabeth Monroe |
| 30 June 1768 | Elizabeth Kortright born (future Mrs James Monroe) |
| June 1774 | began studies at College of William and Mary |
| 1774 | Spence Monroe (father) died inherited farm in Westmoreland County |
| February 1776 | commissioned lieutenant in 3rd Virginia Infantry |
| 16 September 1776 | at Battle of Harlem Heights |
| 28 October 1776 | at Battle of White Plains |
| 26 December 1776 | wounded at Battle of Trenton |
| July 1777 | promoted to captain |
| 11 August 1777 | began serving as aide-de-camp to General Stirling |
| 11 September 1777 | at Battle of Brandywine |
| 4 October 1777 | at Battle of Germantown |
| 20 November 1777 | promoted to major |
| January-June 1778 | at Valley Forge |
| 28 June 1778 | at Battle of Monmouth |
| 20 December 1778 | resigned from the Continental Army |
| 15 August -15 December 1779 | lieutenant-colonel in Virginia State Line assigned to Williamsburg |
| January 1780 | began to study law with Thomas Jefferson |
| June-August 1780 | with army in North Carolina as observer for Governor Jefferson |
| 4 April 1782 | elected to Virginia House of Delegates from King George County |
| June 1782 | admitted to bar |
| 7 June 1782 | appointed to Council of State of Virginia |
| 6 June 1783 | elected to Continental Congress |
| July-October 1784 | tour of Great Lakes and Canada |
| 25 August -14 November 1785 | trip to Kentucky |
| 16 February 1786 | married Elizabeth Kortright in New York |
| April 1786 | lost election to Virginia House of Delegates |
| 13 October 1786 | term in Congress ended |
| October 1786 | established residence in Fredericksburg, VA opened law office |
| December 1786 | Eliza Monroe (daughter) born |
| April 1787 | elected to Virginia House of Delegates from Spotsylvania County |
| 2-27 June 1788 | member Virginia constitutional ratifying convention & voted against ratification |
| October 1788 | purchased farm in Albemarle County, VA became resident of Albemarle County |
| 2 February 1789 | James Madison defeated Monroe in election to House of Representatives |
| 9 November 1790 | elected to U.S. Senate |
| 1793 | purchased another farm in Albemarle County (later named Highland) |
| 28 May 1794 | appointed minister to France |
| 30 December 1796 | mission to France ended |
| August 1797 | returned to Charlottesville began construction of house at Highland returned to law practice |
| May 1799 | James Spence Monroe (son) born |
| 23 November 1799 | established residence at Highland |
| 17 December 1799 | elected governor of Virginia |
| 28 September 1800 | James Spence Monroe died |
| April 8 1802 |
Maria Hester Monroe (daughter) born |
| September 1802 | Elizabeth Monroe Buckner (sister) died |
| 9 December 1802 | term as governor ended |
| 12 January 1803 | appointed minister extraordinary to France |
| 2 March 1803 | appointed minister extraordinary to Spain |
| 18 April 1803 | appointed minister to Great Britain |
| 30 April 1803 | signed Louisiana Purchase treaty |
| 1 January 1805 – 26 May 1805 | in Madrid for treaty negotiations |
| 31 December 1806 | signed treaty with Great Britain not accepted by President Jefferson |
| November 1807 | mission to Great Britain ended |
| 21 January 1808 | nominated for president by dissident Republicans in Virginia |
| July-August 1808 | trip to Kentucky |
| 28 September 1808 | Eliza Monroe married George Hay |
| 1808 | acquired Oak Hill in Loudoun County, VA |
| April 1810 | elected to Virginia House of Delegates from Albemarle County |
| 18 January 1811 | elected governor of Virginia |
| 2 April 1811 | appointed secretary of state |
| 19 December 1812 – 5 February 1813 | acting secretary of war |
| 27 August 1814 | appointed secretary of war serves concurrently as secretary of state |
| 15 March 1815 | resigned as secretary of war |
| October 1816 | appointed to board of visitors for Central College (University of Virginia) |
| 4 March 1817 | inaugurated as president |
| 20 April 1817 | Rush-Bagot Treaty signed |
| June – September 1817 | tour of northern states |
| 6 October 1817 | presided at laying of cornerstone of University of Virginia |
| April-May 1818 | Jackson’s invasion of Florida |
| May-June 1818 | tour of Chesapeake Bay area |
| 20 October 1818 | US-Canadian border treaty |
| 25 February 1819 | signed Adams-Onis Treaty |
| April-July 1819 | tour of southern states |
| 1819 | began construction of new house at Oak Hill |
| 3 March 1820 | Missouri Compromise |
| 9 March 1820 | Maria Hester Monroe married Samuel Gouverneur |
| 5 March 1821 | inaugurated for second term as president |
| 8 March 1822 | recommended recognition of South American republics |
| 2 December 1823 | delivered annual message containing Monroe Doctrine |
| 6 August 1824 | Joseph J. Monroe (brother) died |
| 4 March 1825 | presidency ended |
| ca. 25 March 1825 | retired to Oak Hill in Loudoun County |
| 1 August 1826 | appointed to board of visitors of University of Virginia |
| 24 Oct 1826 | declines appointment as delegate to convention of American nations in Panama |
| 2 December 1826 | Andrew Monroe (brother) died |
| January 1827 | declined to be candidate for election as governor of Virginia |
| December 1827 | declined to be candidate for election as vice president |
| July 1828   ; |
sold Highland |
| 5 October- 12 December 1829 | president of Virginia constitutional convention |
| 21 September 1830 | George Hay (son-in-law) died |
| 23 September 1830 | Elizabeth Kortright Monroe died |
| October 1830 | moved to New York City |
| 14 May 1831 | resigned from board of visitors of University of Virginia |
| 4 July 1831 | died in New York |
