Over the course of the seventeenth century, the English and the French battled each other in upstate New York and Canada for control of the New World. On October 24th, 1690, the English failed in their first attempt to push the French out of America, when Sir William Phips, the commander of a British fleet then laid up in the St. Lawrence River besieging the French Canadian city of Quebec, was forced to concede defeat. It was to prove the first, but not the last, setback for British American colonists in their efforts to oust the French from North America.

The Phips expedition of 1690 was the first American attempt to capture Canada, and undoubtedly the riskiest. Just a decade earlier, the French in Canada had been official allies of British Americans, standing together to keep the Dutch and the Spanish out of the Americas. Trade had boomed between the settlements of Montreal and Quebec along the St. Lawrence River valley, and Boston, New York, and Philadelphia on the continental coast. Though the violence and disruption of King Philip’s War in 1676 had affected relations between British Americans and those Native American tribes allied to the French on the Maine frontier, peace, for the most part, reigned in the 1680s. In that decade, William Phips, a shipbuilder born in what is today Woolwich, Maine, made his way to the Caribbean to seek his fortune diving for treasure amongst Spanish wrecks. Success in 1687 off the coast of Hispaniola made him and his business partners very wealthy, for which Phips was rewarded with a knighthood and a position in the royal government in Boston in return for turning over 25% of the spoils to King James II.

Upon his arrival in Boston, however, Phips – dubbed “The New England Knight” by his friends and admirers – quickly clashed with the royal governor, Edmund Andros, and lent support to the governor’s political enemies, particularly the influential Puritan father-and-son duo of Increase and Cotton Mather. In 1689, news arrived from England that James II had been toppled and replaced by the Dutch Prince William III – an event contemporaries were already dubbing the “Glorious Revolution” – and New England descended into chaos. Colonists threw Andros out of office, accusing him of leaving the colony unprepared for a possible attack from French Canada or from France’s Indian allies. The uprising was led by Boston’s ministers and merchants and backed by New York’s wealthy landowners, and their complaints proved prophetic when Micmac and Iroquois warriors began raiding the Maine and New York frontiers in the early months of 1690.

Amid this maelstrom, the provisional government that took over Massachusetts after Andros’s fall appointed Sir William Phips to head a military expedition against the French. Colonial officials mustered more than 2,000 men and 34 warships, many of which were repurposed merchant sloops and brigantines. They also planned a land expedition of 800 New Yorkers and Iroquois warriors loyal to New York, commanded by Capt. John Schuyler of Albany, to strike at Montreal from the south through the Green Mountains.

These preparations astonished the French governor in Quebec, Louis Frontenac, whose city did not even possess siege defences against a possible invading army. The Phips expedition broke the previous pattern of military engagement in North America: previously, England and France had been careful to clash only proxy armies made up of Indian allies and colonial frontiersmen. That British colonists could muster troops and ships so quickly for an attack on French Canada was a rude awakening for officials in Quebec, especially after Port Royal fell quickly to Phips and his forces when they reached Nova Scotia on May 21, 1690. The French caught a break, however, when inadequate supplies and a smallpox outbreak saw Capt. Schuyler’s Iroquois allies abandon his land advance and forced him to return to Albany unbloodied. The 300 French troops who had been garrisoned in Montreal to repel the aborted attack rushed to help defend Quebec, considerably boosting the city’s defences.

Sir William Phips’s forces left Port Royal for Quebec late in the season, in part because they hoped—forlornly– to be resupplied with munitions from England. The perishing nights and chill winds of autumn on the St. Lawrence meant that by October 16th, when they arrived before Quebec, they had already lost hundreds to illness. They found the city unexpectedly well fortified, and had trouble landing on the banks of the river where Frontenac’s Indian allies harassed them. By October 19, Phips’s ships had exhausted their munitions, but French batteries continued to pound the vessels until the 23rd. By the 24th, it was clear that the American forces could not take the city. Phips negotiated a prisoner exchange with Frontenac and ordered his ships home to Boston, becoming the first, but certainly not the last, British commander chastened by defeat in French Canada. It would not be until 1759, almost 70 years later, that a full-scale British military expedition led by General James Wolfe would capture Quebec and forced the French out of the New World, finally accomplishing what the New England Knight had set out to do in 1690.