Dorchester Heights – 1776

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Dorchester Heights – 1776

That Dorchester Heights could decide the whole outcome at Boston had been apparent to the British from the beginning. Their initial plan, agreed to on June 15, had been to seize the high ground on both the Charlestown and Dorchester peninsulas. But then the rebels had made their surprise move at Charlestown, digging in overnight on Bunker Hill, and it had taken the bloodbath of June 17 to remove them. The morning after the battle, in a council of war at the Province House, headquarters of the commander-in-chief, Thomas Gage, it was proposed by Major General Henry Clinton to move immediately on Dorchester. Possession of the heights was “absolutely necessary for the security of Boston, as they lay directly on our water communications and more seriously annoyed the port of Boston than those of Charlestown,” Clinton later wrote, adding that he expected to lead the assault. “I foresaw the consequence, and gave it formally as my opinion at the time, that if the King’s troops should be ever driven from Boston, it would be by rebel batteries raised on those heights.”

But while Gage had kept Bunker Hill heavily armed with cannon and manned by five hundred troops, he had done nothing about Dorchester. Nor had General Howe since taking charge after Gage’s departure for home in October. Nor, indeed, had the Americans. Dorchester Heights remained a kind of high, windblown no-man’s-land, neither side unmindful of its strategic importance, but neither side daring to seize and fortify it.

Among those Loyalists in Boston who had closest contact with the British command, it was commonly understood that Dorchester was the key and commonly questioned why nothing was being done. “It had often been wished,” wrote Justice Peter Oliver, one of the most prominent Loyalists, “that this hill had had proper attention paid to it; and it had been repeatedly mentioned that it was of the last necessity to secure such a position; but the general answers were that there was no danger from it, and that it was to be wished that the rebels would take possession of it, as they could be dislodged.”

Of greater and more immediate interest to the British command was the prospect of abandoning Boston altogether, of packing up and sailing away. As things stood, it was clearly no place to launch an offensive operation. New York should be made the “seat of war,” Gage had stressed in correspondence with the administration in London, and Howe and the others were of the same opinion.

Brigadier General James Grant had said months earlier that Boston should be abandoned while there was still time. “We cannot remain during the winter in this place, as our situation must go on worse and that of the rebels better every day,” Grant had insisted in a long letter from Boston to Edward Harvey, Adjutant General of the British army in London, on August 11.

Grant, a grossly fat, highly opinionated Scot, who had served in the French and Indian War, had an extremely low opinion of Americans. (It was he who had boasted to Parliament that with 5,000 men he could march from one end of the American continent to the other.) The only step that made sense, he wrote, was to burn Boston and move on to New York. Besides, he wanted to turn the fleet loose to burn every principle town along the New England coast. “Lenity is out of the question.”

Such were the delays in communication across the ocean that by the time General Howe received orders from London to “abandon Boston before winter” and “remove the troops to New York,” it was too late—winter had arrived. Besides, there were too few ships at hand to transport the army and the hundreds of Loyalists about whom Howe was greatly concerned, knowing what their fate could be if they were left behind.

Seeing no reasonable alternative, Howe would wait for spring when he could depart at a time and under conditions of his own choosing. He expected no trouble from the Americans. “We are not under the least apprehension of an attack on this place from the rebels by surprise or otherwise,” he assured his superiors in London and further stressed the point at a meeting with his general staff on December 3. Should, however, the rebels make a move on Dorchester, then, Howe affirmed, “We must go at it with our whole force.”

Quite unlike the man in command of the army encircling the town, the British commander was not impatient for action. On the contrary, William Howe had little inclination ever to rush things. Further, it was taken as a matter of course among professional soldiers that winter was no season for campaigning.

And so the British army settled in for a long Boston winter, seeing to their comforts as best they could under the circumstances.

The notable exception was Major General John Burgoyne, “Gentleman Johnny,” an officer of distinguished record and occasional playwright who had added welcome color to the social life of the British officers and their ladies. Impatient with “supineness,” as he said, and ambitious for a command of his own, Burgoyne had sailed for England in early December.


Winter in America was a trial British soldiers could never get used to, any more than they could adjust to the incessant clamor of frogs on spring nights or American mosquitoes or the absence of decent beer. The harsh winter winds and driving snows of the bay area inflicted misery indiscriminately on both armies, of course, but for the King’s men, unaccustomed to such a climate, the punishment was all but unbearable. A young Irish nobleman, Captain Francis Lord Rawdon, wrote of the suffering of his men encamped on Bunker Hill in early December, their tents “so shattered” they could as well have slept on the open ground—“and we hear with some envy of several little balls and concerts which our brethren have had in Boston.” Soldiers froze to death standing watch. Even when the troops moved to winter quarters a few weeks later, keeping warm seemed nearly impossible.

The open sea remained the only lifeline for fuel and food for the town, but with the severity of storms on the North Atlantic, and American privateers operating offshore in increasing numbers despite the weather, fewer and fewer supply ships were getting through. (“The rebels have the impudence to fit out privateers,” wrote an indignant British officer, snug in his quarters, but the day would come, he knew, when “we shall give the scoundrels a hearty thrashing and put an end to this business.”)

British Admiral Samuel Graves, whose responsibility it was to patrol the coastline against privateers, described snowstorms at sea between Cape Ann and Cape Cod as defying the most resolute of men.

This sort of storm is so severe that it cannot even be looked against, and by the snow freezing as fast as it falls, baffles all resistance—for the blocks become choked, the tackle encrusted, the ropes and sails quite congealed, and the whole ship before long one cake of ice…. Indeed, if the severity of the winters be such in this climate that the sentinel on shore is frequently found frozen to death upon his post, though relieved every half hour, the reader may frame some idea of what the seamen of a watch, especially in small vessels, must suffer.

With firewood selling for $20 a cord in Boston, more and more trees were cut down, including the old elm at the corner of Essex and Orange streets, known as the Liberty Tree, which provided fourteen cords. A hundred or more houses were pulled apart. Old barns, old wharves, and derelict ships were chopped up, almost anything that would burn. On orders from General Howe, Old North Church was demolished for firewood.

Only a fraction of Boston’s former, peacetime population remained, thousands having long since fled the town. But others, Loyalists, had sought refuge there, and Loyalists were conspicuous, if not necessarily more numerous than those inhabitants who had chosen to stay in the hope of protecting their property, or because they were too poor or helpless to do anything else. A few, like the town’s selectmen, had been forbidden to leave. In all, there were now about 4,000 civilians under siege, at least half of whom were women and children, and they, too, no less than the redcoat army, were hurting from shortages of all kinds, the poor inevitably suffering most.

Food remained extremely scarce and dear. Young Lord Rawdon described his famished troops as looking like skeletons. Even inferior cuts of horse meat brought good prices. To put a stop to increasing instances of plunder by the troops, Howe initiated punishments more severe even than the standard for the British army. In fact, the new year of 1776 began in Boston with the public whipping of a soldier and his wife who had been caught with stolen goods.

For the British officers, however—the “redcoat gentry,” as Washington called them—life was not entirely unpleasant. They had appropriated Old South Church for a riding ring—Old South Church being odious to them because town meetings had been held there. (Pews were torn out, dirt spread on the floor. According to the diary of Deacon Timothy Newell, one particularly beautiful, hand-carved pew was taken away to serve as a hog sty.) Evening entertainments were numerous. “We have plays, assemblies, and balls, and live as if we were in a place of plenty,” wrote an officer. “In the midst of these horrors of war, we endeavor as much as possible to forget them,” explained the wife of another officer in a letter to a friend at home.

Writing again to General Harvey, James Grant said, “We must get through a disagreeable winter the best way we can. I do all in my power to keep the ball up—I have all ranks of officers at dinner, give them good wine, laugh at the Yankees and turn them into ridicule when an opportunity offers.”

Boston having no theater, Faneuil Hall, sacred to Boston patriots as “the cradle of liberty,” was converted on General Howe’s wish into a “very elegant playhouse” for amateur productions of Shakespeare and original farces, with officers and favored Loyalists taking parts. Sally Flucker, the sister of Henry Knox’s wife, Lucy Flucker, for example, took a lead part in a production of Maid of the Oaks, a satire by General Burgoyne.

On the evening of January 8, uniformed officers and their ladies packed Faneuil Hall for what was expected to be the event of the season, a performance of a musical farce said also to have been written by Burgoyne. Titled The Blockade, it was off to a rollicking start from the moment the curtain rose. A ridiculous figure, supposed to be George Washington, stumbled on stage wearing an oversized wig and dragging a rusty sword. At the same moment, across the bay, Connecticut soldiers led by Major Thomas Knowlton launched a surprise attack on Charlestown, and the British responded with a thunderous cannon barrage. With the roar of the guns, which the audience at Faneuil Hall took to be part of the show, another comic figure, a Yankee sergeant in farmer garb, rushed on stage to say the rebels were “at it tooth and nail over in Charlestown.” The audience roared with laughter and “clapped prodigiously,” sure that this, too, was part of the fun.

But soon finding their mistake [wrote an eyewitness] a general scene of confusion ensued. They immediately hurried out of the house to their alarm posts, some skipping over the orchestra, trampling on the fiddles, and, in short, everyone making his most speedy retreat, the actors (who were all officers) calling out for water to get the paint and smut off their faces, women fainting, etc.

Reportedly, it was General Howe himself who shouted, “Turn out! Turn out!”


The British Commander, an easy-going, affable man who had never been averse to taking his pleasures when he could, was openly enjoying himself through the winter with his own elegant dinners, extended evenings at the faro table, and conspicuously in the company of a stunning young woman about whom there was much talk. The lady, who was to become known as Billy Howe’s Cleopatra, was Elizabeth Lloyd Loring, the wife of Joshua Loring, Jr., a member of a prominent Loyalist family whom Howe had hired to run the commissary for rebel prisoners. In the words of a contemporary Loyalist chronicler of the war, “Joshua had a handsome wife. The general…was fond of her. Joshua had no objections. He fingered the cash, the general enjoyed madam.”

William Howe had been a professional soldier from the time he finished school at Eton and at age seventeen received a commission in the Duke of Cumberland’s Light Dragoons. Two older brothers had also chosen military careers and distinguished themselves. The oldest, George Augustus Lord Howe, had fought and died in America in the French and Indian War and was remembered in New England as one of the bravest, best-loved British officers of the time. The other brother, Richard—Admiral Lord Howe—had begun his career in the Royal Navy at fourteen. Like William, he was a member of Parliament and much admired by the King.

The Howe brothers belonged to one of England’s most eminent families. They were rich, accomplished, and extremely well connected. Their mother, still a force in London society, was said to be the illegitimate daughter of King George I. Both men were staunch Whigs and had a decided resemblance, a rather gloomy, dark look, with dark eyes, heavy lids, and a swarthy complexion. But the general was the taller, at about six feet, the heavier, and a man of fewer words. In Parliament he rarely spoke. To Horace Walpole, Billy Howe was “one of those brave silent brothers [who] was reckoned sensible, though so silent that nobody knew whether he was or not.” Nor was it clear how much real heart the general had for the war in America, given his earlier comments about having no wish to serve in it.

William Howe’s ability and courage were indisputable. As a heroic young lieutenant colonel in the French and Indian War, he had led a detachment of light infantry up the steep embankments of Quebec in the first light of dawn to make way for the army of General James Wolfe to defeat the French under Montcalm on the Plains of Abraham. Wolfe had called William Howe the best officer in the King’s service. At Bunker Hill, assuring his troops he would not ask them “to go a step further than where I go myself,” he had marched in the front line. When the men fell back, after the slaughter of the first assault, he led them up the hill twice again. After one blinding volley during the third assault, he had been the only man in the front line still standing.

But for all his raw courage in the heat and tumult of war, Billy Howe could be, in the intervals between actions, slow-moving, procrastinating, negligent in preparing for action, interested more in his own creature comforts and pleasures.

That he had been stunned by the terrible cost of British victory at Bunker Hill there is no question. “The success is too dearly bought,” he had written to his brother the admiral. Still, he was a soldier, a gifted strategist, and a fighter. He liked to tell his troops, “I do not in the least doubt but that you will behave like Englishmen and as becomes good soldiers,” and he expected no less of himself. He would be a good soldier always, whenever put to the test. He meant business, and at forty-five, or approximately the same age as George Washington, he had far greater experience than Washington, a far more impressive record, not to mention better-trained, better-equipped troops, and ships of the Royal Navy riding at anchor in the harbor.

He also had the ostensible advantage of experienced subordinate officers, professionals all, several of whom had marked ability. When, in the previous spring, Howe, Clinton, and Burgoyne had sailed from England for the war in America, they truly represented the pick of the King’s officers. All three were men of proven courage and commitment to duty. Like Howe, Clinton and Burgoyne were well-connected, well-schooled aristocrats, and, as major generals, at the threshold of the peak years of their careers. Clinton, Howe’s second-in-command, was the least impressive in appearance, a short, fat, colorless man who could be shy and petulant. But he had a keen military mind and the advantage of knowing Americans from boyhood. He had grown up in New York, where his father, Admiral George Clinton, served as governor from 1741 to 1751.

Among those of lesser rank, an outstanding example was John Montresor, an officer of engineers whose years of service and experience would seem to make a mockery of the very idea that someone like Nathanael Greene could be a major general. Montresor, too, had served in the French and Indian War, in the Braddock campaign and at Wolfe’s siege of Quebec. In 1760, at age twenty-four, he had led a winter expedition overland from Quebec to New England, and at the war’s end worked on fortifications from Boston to Detroit to New York City, where he bought an island, Montresor’s Island, in the East River. He was resourceful, energetic, probably the best engineer in the British army, and with experience in America to equal any.

But it was also true that Howe and Clinton disliked one another and did not work well together, and that John Montresor, who was not an aristocrat, was still, at nearly forty, only a captain. If the desperate American need for leaders had thrust young men like Nathanael Greene into positions beyond their experience, the British military system, wherein commissions were bought and aristocrats given preference, denied many men of ability roles they should have played. Had Captain John Montresor been a major general, the outcome of the struggle might have been quite different.

Howe’s sources of intelligence, furthermore, were pitiful, virtually nonexistent. As near at hand as the rebels were, the British commander knew almost nothing of their true situation, their perilously thin lines, their lack of gunpowder. Bunker Hill had taught Howe not to underestimate his foe. Still, he had no doubt that the “present unfavorable appearance of things” could be rectified readily enough. All that was wanting was a “proper army” of 20,000.

In mid-January, on orders from London, General Clinton and a small fleet sailed away southward to see what advantage might be gained in the Carolinas, thus reducing the British force at Boston by 1,500 men. And, as pleased as Howe may have been to see Clinton leave, Clinton had at least served as an antidote to Howe’s “supineness.”

Oddly, Howe seems to have had no interest in the man who led the army aligned against him. In all that he and others of the British command wrote at the time, officially and privately, George Washington was rarely ever mentioned except in passing. There was no apparent consideration of what manner of man he was, what his state of mind, his strengths and weaknesses, might be. Or what he might be up to, given the working of his mind. Perhaps this was indifference, perhaps the measure of an overreaching sense of superiority. Washington, by contrast, was constantly trying to fathom Howe’s intentions, his next move. Strange it was that the British commander-in-chief, known for his chronic gambling, seemed to give no thought to how his American opponent might play his hand.

Forschungsmitarbeiter Mitch Williamson is a technical writer with an interest in military and naval affairs. He has published articles in Cross & Cockade International and Wartime magazines. He was research associate for the Bio-history Cross in the Sky, a book about Charles ‘Moth’ Eaton’s career, in collaboration with the flier’s son, Dr Charles S. Eaton. He also assisted in picture research for John Burton’s Fortnight of Infamy. Mitch is now publishing on the WWW various specialist websites combined with custom website design work. He enjoys working and supporting his local C3 Church. “Curate and Compile“
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