Like many of the Revolutionary generation, James Monroe was born to humble beginnings in the underdeveloped colonies of the New World. The Monroe family had arrived in America in 1650; his ancestor, Andrew Monroe, was a captain in the army of Charles I of England and many sources agree that he fled the British Isles soon after the king was beheaded. However, a few sources differ, stating that he was captured by the revolutionary forces and exiled to the new colonies. In any event, historians agree that the Monroe ancestral family settled near a creek in Virginia. By the time James Monroe was born in Westmoreland County, VA, on April 28, 1758, much of the land surrounding his family farm belonged to other relatives. The farm was located on the fertile right bank of the Potomac River, near the Rappahannock River, on what was quite possibly the best land in Virginia for farming.

James's father, Spence Monroe, and his mother, Eliza Jones, had been born and raised in Virginia–in an area now famous for the children it gave the country. George Washington's birthplace was not far away; Richard Henry Lee and the Lee family lived nearby; James Madison's birthplace, although not in the same county, was on the same peninsula. Later, Westmoreland County would come to be known as the "Athens of Virginia," for the wise scholars and notable families who lived nearby.

Growing up, Monroe enjoyed many of the luxuries of the planter lifestyle: good food and entertainment and the best education that money could buy. When he was eleven, he entered one of Virginia's most prestigious schools, the Campbelton Academy, where he studied for five years. He worked hard and excelled at reading and writing; his favorites subjects, though, were math and Latin. He also met a life-long friend at Campbelton, John Marshall, and the two boys consistently battled for the top spots in the class. Marshall would later become perhaps the most famous Chief Justice of the U.S. Supreme Court, after being appointed by John Adams in the "midnight judges" scandal.

Despite his high academic achievement, Monroe found his education and his own youth overtaken by outside events. When he was five years old, the English government–which had for decades neglected the colonies–signed a peace treaty ending the French and Indian War. However, after the long and costly battle, the financially-strapped British Parliament decided that the American colonies should begin to bear some of the burden of defending themselves. A series of Parliamentary Acts, beginning with the Sugar Act (which raised duties on formerly duty-free wines), caused increasing outrage throughout the colonies. This patriotic fervor was concentrated mostly in Boston and Virginia, where "rabble-rousers" like Samuel Adams and Richard Henry Lee respectively, pushed the Americans to fight back against the "unjust" taxes. In the wake of the even- more controversial Stamp Act, the Virginia House of Burgesses passed the Virginia Resolves, which denied that Parliament had a right to tax the colonies. The Resolves, coupled with similar measures in other legislatures and the development of committees of correspondence to coordinate actions between colonies, put the American colonies on the road to revolution. Monroe found himself greatly influenced by the civil libertarians around him.

Monroe lost both of his parents within a span of only a few months in 1774. Following the colonial traditions, Monroe–barely sixteen–inherited the family farm and became responsible for his older sister and three younger brothers. His uncle, the executor of his father's will, removed him from Campbelton Academy and placed him at William and Mary College, the nation's second oldest college, in Williamsburg. Again, outside events quickly overtook Monroe's education, and in the spring of 1775, British troops opened fire on colonial minutemen at Lexington and Concord, firing "the shots heard round the world." Monroe and some college classmates, caught up in the anti-British spirit, looted the arsenal at the Virginia Crown Governor's palace; the two hundred muskets and three hundred swords they captured were donated to the Virginia militia. With the Second Continental Congress meeting in Philadelphia, and with Washington's troops bloody fight at Bunker Hill in Boston, it was clear that war–a long, hard war–was underway.

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