| 1755 | Stuart is born in Kingston, Rhode Island. |
| 1769 | Stuart becomes apprentice to a Scottish portraitist in Newport. |
| 1772 | Stuart lives in Scotland for a year. |
| 1775 | American Revolution begins with the battles of Lexington and Concord. Stuart moves from Newport to London. |
| 1776 | The Continental Congress adopts The Declaration of Independence in Philadelphia. |
| 1777 | Stuart enters Benjamin West’s studio in London. |
| 1781 | British troops surrender to American forces at Yorktown. |
| 1782 | Stuart, in London, gains recognition with The Skater. |
| 1783 | Treaty of Paris is signed, establishing peace between the new United States and England. Stuart receives a commission for portraits of fifteen London artists, including Reynolds, West, and Copley. |
| 1786 | Stuart marries Charlotte Coates, the daughter of an English doctor. |
| 1787 | Stuart moves to Dublin and enjoys great success in the Irish capital. |
| 1789 | George Washington is inaugurated as first president. The first session of the United States Congress meets in New York. Stuart is briefly imprisoned in Dublin for debts. |
| 1790 | The federal capital is transferred from New York to Philadelphia. |
| 1793 | Washington begins his second term as president. Stuart returns to the United States and spends more than a year in New York. |
| 1795 | Stuart paints his first portrait of George Washington in Philadelphia. |
| 1797 | John Adams is inaugurated as second president; Washington retires to Mount Vernon. |
| 1799 | Death of Washington |
| 1800 | The federal capital is transferred to Washington, DC. |
| 1801 | Thomas Jefferson is inaugurated as third president. |
| 1803 | President Jefferson negotiates the Louisiana Purchase. Stuart moves to Washington, DC. |
| 1805 | Stuart settles in Boston for the remainder of his life. |
| 1809 | James Madison is inaugurated as fourth president. |
| 1812 | War with Great Britain breaks out. |
| 1814 | British troops enter Washington, DC, and burn the White House; a peace treaty is signed at the end of the year. |
| 1817 | James Monroe is inaugurated as fifth president. |
| 1821 | Stuart receives a commission from John Doggett to paint a series of portraits of the first five presidents. |
| 1825 | John Quincy Adams is inaugurated as sixth president. |
| 1828 | Stuart dies, leaving his family poverty stricken. Philadelphia artists wear black armbands for a month. |
