New York’s Underdogs Prepare to Fight

As part of our celebration of America at 250, we’ve started a weekly newsletter by historian Jonathan Horn. Learn what happened this week in American history, why it matters, and what else you should see and read in The Free Press and beyond. Sign up here. This week, Jonathan looks at the day that the British fleet descended on New York. —The Editors

When John Adams pictured how future generations of Americans would celebrate the anniversary of their independence, he foresaw parades, shows, fireworks, and, yes, even sporting events (he had tried his hand at wrestling and boxing in his youth). What Adams couldn’t have imagined was that among the most anticipated spectacles a quarter of a millennium later would be the one that General George Washington and his soldiers most dreaded in June 1776: the arrival of a massive armada of tall-masted sail vessels in the waters around New York City.

As scores of ships make their way to the Big Apple for this year’s Sail4th 250 celebration (organizers are billing it as “the largest-ever flotilla of tall ships from around the world”), be sure to spare a thought for the patriots manning lookouts around the city 250 years ago this June when the British fleet came into view.

More than three months had passed since the Continental Army had forced British general William Howe and his men to evacuate Boston. They had sailed north for Halifax, Nova Scotia, where they had stayed aboard their ships in conditions historian Andrew Jackson O’Shaughnessy describes as “cramped and freezing,” except when Howe took soldiers ashore to drill for their next mission: an offensive against New York City. When it came time for the fleet to sail there in early June, the redcoats were well-trained and bent on revenge. “It is become highly necessary that the first exertion of the army should be directed to the most important purposes: to check the spirit which the evacuation of Boston will naturally raise among the rebels,” Howe wrote. The destruction of the Continental Army, he believed, would serve the purpose nicely.