The preparations for the advance to Dorchester Heights had begun the previous morning as Quartermaster Mifflin supervised the organization of more than 350 oxen carts. Sunset was at 5:35, and it soon proved to be the perfect night: a low-lying haze prevented the British from seeing much of anything beyond Boston as a full moon provided the Americans with the light they needed to find their way to Dorchester, and a southerly wind blew whatever noise the soldiers made “into the harbor between the town and the Castle.”
At 7:00 p.m., two “covering parties” of four hundred soldiers each crossed the Neck into Dorchester and, after mounting the heights, took up positions where they could watch for the British soldiers both in Boston and at the Castle. Next came General Thomas with a work party of approximately twelve hundred soldiers, followed by the wagons, each driver urging his oxen “in a whispering tone.” Soon a total of three thousand of what Thomas described as “picked men” were at work, laying huge bundles of hay along the Neck to act as a screen, and once on the Heights, assembling two different forts—one facing the Castle, the other facing Boston. The chandeliers were quickly arranged and the fascines put in place as the men went to work with their picks and shovels, digging ditches and hurling the frozen clods of dirt onto the breastworks. They labored with astonishing speed and efficiency, and after only a couple hours’ work, as the carts continued to go back and forth in silence, General Thomas was pleased to note that “they had got two forts, one upon each hill, sufficient to defend them from small arms and grape shot.” He took out his pocket watch and was amazed to discover that it was only ten o’clock. As it so happened, at almost precisely the same time, the British sentinels in Boston relayed word to Brigadier General Francis Smith (who had received a promotion since leading his troops to Concord a little less than a year before) that “the rebels were at work on Dorchester Heights.” As on the night before the Battle of Bunker Hill, no one within the British leadership chose to act on the information.
The next morning the British were astounded to see two towering forts atop the hills of Dorchester. “They were all raised during the night,” an awestruck officer wrote, “with an expedition equal to that of the Genii belonging to Aladdin’s wonderful lamp.” Thanks to the magnifying effect of the haze that lay on the land and water, the American works “loomed to great advantage and appeared larger than the reality.” The minister William Gordon later learned that “Howe was seen to scratch his head and heard to say by those that were about him, that he did not know what he should do, that the provincials . . . had done more work in one night than his whole army would have done in six months.” The engineer Archibald Robertson estimated that the fortifications must have been the work of between fifteen thousand and twenty thousand men.
The rumor among the Americans was that Howe had long since vowed that should they dare to “break ground” on Dorchester Heights he would “sally on us [even] if he was sure of losing two-thirds of his army.” As the soldiers atop Dorchester Heights waited to see whether Howe was as good as his supposed word, the British batteries began firing at the new forts. The surgeon James Thacher was with the soldiers on the Heights. “Cannon shot are continually rolling and rebounding over the hill,” he wrote in his diary, “and it is astonishing to observe how little our soldiers are terrified by them.” But the British artillerymen had a problem. Dorchester Heights was simply too high for them to fire at it effectively. “They endeavored to elevate their cannons so as to breach our works by sinking the hinder wheels . . . into the earth,” General John Sullivan wrote, “but after an unsuccessful fire of about two hours, they grew weary of it and desisted.”
Even before the cessation of artillery fire, onlookers began to make their way to Dorchester. “The hills and elevations in this vicinity are covered with spectators,” James Thacher reported, “to witness deeds of horror in the expected conflict.” All of Boston lay before them. “Nothing could take place at the wharves or next to the water,” one observer wrote, “but we could note it by the help of glasses.” It certainly looked as if Howe were preparing to attack. “The wharf was thronged with soldiers,” wrote William Gordon, who along with Thacher was “looking upon the adjacent hills for a bloody battle.” As the regulars boarded transports and were taken to the Castle, the natural staging ground for an attack, the Americans on Dorchester Heights “rejoiced at seeing it, clapped their hands and wished for the expected attack.”
Their British counterparts were not as enthusiastic. A Boston resident later recounted how the regulars lined up along the town’s streets “looked in general pale and dejected and said to one another that it would be another Bunker’s Hill affair or worse.” In anticipation of scaling the American bulwarks, they collected ladders and cut them into ten-foot lengths.
The optimum time for a British attack was at high tide, which was at two that afternoon, and the Americans watched with mounting excitement to see whether Howe dared to go through with it. By this time Washington had appeared on the Heights and was overheard exhorting, “Remember it is the fifth of March!” and “Avenge the death of your brethren!” “It was immediately asked,” William Gordon wrote, “what the general had said by those that were not near enough to hear, and as soon answered; and so from one to another through all the troops, which added fresh fuel to the martial fire before kindled.”
All the while, on the other side of the Boston peninsula, four thousand American soldiers under the commands of Generals Putnam, Sullivan, and Greene were waiting at the mouth of the Charles River, ready to climb into their boats and begin the assault of the city. Greene and half the troops were to land just to the south of Barton’s Point at the northwestern tip of Boston; Sullivan was to come ashore at the Boston Common; both were to fight their way through the city until they reached the town gate and joined their compatriots coming in from Roxbury.
But as it turned out, Howe had decided to delay the move on Dorchester Heights until the following morning. That night the surgeon James Thacher’s regiment, which had been on station for the last twenty-four hours, was allowed to return to their barracks in Roxbury for some rest. “I bade adieu to Dorchester Heights,” he recorded in his journal in the early morning hours of March 6, “without being called to dress a single wound.”
For William Howe and his officers, it proved to be a most tension-filled evening and night. Archibald Robertson, for one, believed that the general was making a terrible mistake by even considering an attack. The American works atop the Heights were simply too formidable. Instead of mounting an assault, “we ought immediately to embark” and leave Boston. “The fate of this whole army and the town is at stake,” he wrote in his diary at four that afternoon, “not to say the fate of America.” After communicating his concerns to every superior officer he could find, he went to Province House, where at 7:00 p.m. Howe and his generals were in the midst of a council of war. Robertson waited outside the door for more than an hour until his commanding officer, the engineer Captain John Montresor, stepped out of the room. Montresor also believed that they had no choice but to evacuate, and he told Robertson that he had said as much during the council of war. He also recounted how “Lord Percy and some others seconded him,” and only then did Howe confess that evacuation had been “his own sentiment from the first” and that it was “the honor of the troops” that had moved him to order an attack. Howe had “agreed immediately,” Montresor continued, “to embark everything.” As Washington’s council of war had done three weeks before, Howe’s officers had prevented their commander from making a decision that might have destroyed both his army and Boston.
If Howe had any lingering doubts when he went to bed that night, the weather decided the matter for all of them. A storm that some judged to be a hurricane blew up out of the south, knocking down buildings and blowing two of the troop transports moored off the Castle onto the shore of nearby Governors Island. Even if Howe had wanted to, he could not have launched an attack on Dorchester Heights
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At eleven the next morning, Howe called together the army’s commanding officers and “acquainted them with his intentions of evacuating this place and going to Halifax.” Washington did not get the chance to attack Boston. Signals had been prepared at the meetinghouse in Roxbury to mark the moment when the amphibious assault was to be launched. “But kind heaven,” William Heath wrote, “which more than once saved the Americans when they would have destroyed themselves, did not allow the signals to be made.”
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On March 8, a British officer bearing a letter from the Boston town selectmen approached the American lines at Roxbury under a flag of truce. General Howe, the selectmen indicated, would not burn the town if the Americans allowed the British to evacuate. This was hopeful news to be sure, but Washington remained fearful that Howe was in fact stalling for time so that he could launch one final thrust against the American forces. As the days passed and Howe’s army remained in Boston, Washington attempted to hurry the British along by building a fortification at Dorchester Heights that was even closer to Boston. Howe responded to each new move on the Americans’ part with artillery fire (in one instance killing several Continental soldiers), and as the day of departure approached, the British general was terrifyingly close to torching the town, a prospect that kept the Bostonians in an unremitting state of apprehension and alarm.
All the while, chaos reigned in the city as the British soldiers struggled to collect as many of their stores as possible for transportation to Halifax. Due to the Admiralty’s almost criminal undermanning of the naval vessels, there was a severe lack of sailors to operate the evacuation fleet. This wasn’t the only problem thrust upon General Howe by his superiors in London. “When the transports came to be examined,” an officer wrote, “they were void of both provisions and forage. . . . Never troops in so disgraceful a situation, and that not in the least to their own fault or owing to any want of skill or discretion in our commanders, but entirely owing to Great Britain being fast asleep. I pity General Howe from my soul.” Dozens of perfectly serviceable sailing vessels were tied up to the wharves, but without the needed sailors and provisions Howe was unable to use them.
The departing British army had no choice but to leave behind a vast amount of heavy armaments and other supplies. To prevent the artillery pieces from being used against them, the soldiers hammered metal rods into the cannons’ touchholes, a procedure known as spiking the guns. As preparations to leave extended into the second week, marauding gangs of soldiers and sailors plundered stores and houses. Howe issued orders that looters be shot on sight, but the stealing continued.
For the region’s loyalists, who had sought sanctuary from patriot reprisals, the decision to evacuate Boston was overwhelming. “The Tories . . . carried death in their faces,” one inhabitant wrote, “some run distracted.” Washington reported that “by all accounts there never existed a more miserable set of beings than these wretched creatures now are. . . . When the order [was] issued for embarking the troops in Boston, no electric shock—no sudden clap of thunder—in a word the last trump—could not have struck them with greater consternation. They are at their wit’s end.”
Howe did what he could to accommodate all those who wanted to accompany his army to Halifax, but once again, there was not enough room for all their furnishings and possessions. In the brigantine Unity was the family of Adino Paddock, the former commander of Boston’s artillery company, along with seven other loyalist households. The outspoken customs commissioner Benjamin Hallowell, the owner of two mansions—one in Boston, the other in Roxbury—found himself sleeping in a cabin with thirty-six others, “men, women, and children; parents, masters, and mistresses, obliged to pig together on the floor, there being no berths.” The province’s treasurer, Harrison Gray, who two and a half years before had admonished Josiah Quincy Jr. for his treasonous words in the Old South Meetinghouse, boarded the Francis, along with thirty-seven others. A total of eleven hundred loyalists divided among thirty vessels ultimately left the wharves of Boston, first sailing past the Castle to the Nantasket Roads at the western end of the harbor, five miles from the city, where they anchored near Paddock and Hull islands and waited for the arrival of the fifty transports bearing the nine thousand soldiers of Howe’s army.
Many of the loyalists would settle in Canada; others went to England. Neither place seemed like home. Some, such as the lawyer Daniel Leonard, who was named chief justice of Bermuda, established new and flourishing careers. A few, such as Dr. John Jeffries, to whom Joseph Warren had offered the position of surgeon general of the provincial army, eventually returned to Boston and through a combination of personal charm and professional ability once again became respected members of the community. But that was decades in the future, and an exception to the rule of forgiveness. Bostonians, like their Puritan forebears, would prove to have long and exacting memories.
By purging itself of loyalists, Boston had, in a sense, reaffirmed its origins. The town’s first settlers had put an ocean between them and their king so that they could worship as they pleased. They were unafraid of risk; otherwise they never would have left England for a new and unknown land. Over the course of the next century and a half, Boston had grown from a settlement of a few hundred Puritans to a diverse and thriving port with a strong commercial connection to London. Many Bostonians, particularly the merchants, had come to cherish their ties to Great Britain. In the last decade, however, a new generation of risk takers had staged a revolution, and those who refused to disavow the mother country were about to sail to Halifax, never to return. Boston was, once again, its own “city on a hill.”
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The engineer Archibald Robertson was one of the last to leave. He had spent the two previous days throwing up barriers across the streets and wharves of Boston to impede the progress of any American soldiers who might try to harass the evacuating regulars. Howe had ordered the town’s citizens to remain confined in their homes so they didn’t interfere with his army’s final preparations to depart. Robertson walked the empty, weirdly quiet waterfront. More than twenty-five brigs, schooners, sloops, and ships had been abandoned, some still full of stores, all of them scuttled. General Gage’s chariot lay broken on Long Wharf. The dragoons had left 110 horses in the stables at the rope walks, along with ten tons of hay. “There seems a vast deal of confusion in every department,” Robertson recorded in his diary, “and no settled plan of operations.”
By 9:00 a.m. on March 17, a Sunday, “all the regiments but the rear guard were embarked.” Robertson, Captain Montresor, and three others lingered on Long Wharf, ready to set fire to a few houses if the enemy should prematurely storm the city, “but none appeared and we went all off in the greatest order.” By ten o’clock he was at the Castle and could see “the rebels on the heights of Charlestown and making a great parade on Dorchester Heights.” As it so happened, March 17 was St. Patrick’s Day, a date celebrated by Irish Protestants in Boston since 1737. Now Bostonians had yet another reason to celebrate March 17, a date that became known as Evacuation Day.
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A young officer named James Wilkinson from Maryland was one of the first into the city. Wilkinson had come via the Charlestown peninsula, where the British had delayed the arrival of the American troops by leaving several “effigies” that looked like regulars with their muskets shouldered. Only after General John Sullivan had determined that the fortress at Bunker Hill was “defended by lifeless sentries” had Wilkinson and the others been allowed to cross the Neck. Near “the ruins of Charlestown . . . now buried in its own ashes,” he’d found a canoe in which he and several others paddled to Boston “on the presumption the enemy had taken their departure.” After disembarking at the waterfront, they’d followed “a long narrow winding street” but were unable to find a living soul to talk to. “The town presented a frightful solitude in the bosom of a numerous population . . . ,” he remembered; “a death-like silence pervaded an i
nhabited city, and spectacles of waste and spoil struck the eye at almost every step.”
Even days later, the three thousand or so Bostonians who had lasted out the siege had a muted, exhausted air about them. James Thacher marched into the city three days after the evacuation. “The inhabitants appeared at their doors and windows,” he wrote; “though they manifested a lively joy on being liberated from a long imprisonment, they were not altogether free from melancholy gloom which ten tedious months’ siege has spread over their countenances.” Two days later, Thacher watched as “a concourse of people from the country crowd[ed] into town, full of friendly solicitude. It is truly interesting to witness the tender interviews and fond embraces of those who have been long separated.”
One of those left pining for a reunion was John Andrews, whose beloved wife Ruthy was not able to return to Boston for several weeks. He missed her terribly, but to his brother-in-law in Philadelphia he asserted that despite all he’d suffered over the course of the last five months, he’d “never suffered the least depression of spirits . . . for a persuasion that my country would eventually prevail, kept up my spirits, and never suffered my hopes to fail.” Andrews’s good mood was no doubt reinforced when at the end of March none other than George Washington, accompanied by Martha and her son and daughter-in-law, came to his house for dinner “with no earlier notice,” he wrote his brother-in-law, “than half past eleven the same day.”