Washington took fateful gamble atop Dorchester Heights

On the night of March 4, 1776, the Patriot officers gave the order to 2,000 or so men: no one was to speak above a whisper. As American batteries opened up on British positions in and around Boston to cloak the long file of Continental troops in “blue and buff” greatcoats or other hues, who lugged timber and cannons as silently as possible through the darkened streets of Roxbury and into Dorchester.

Wincing from the blustery blasts off the Atlantic and from the heft of their ordnance, they pushed ever closer to their objective — Dorchester Heights. If spotted by the redcoat batteries, disaster loomed; if the procession reached the hills, the British regiments in Boston below and the British warships in the harbor and the Charles River would lay wide open to lethal blasts of Colonial artillery from the Heights.

George Washington, the American commander, was rolling the proverbial dice in Dorchester.

Washington had the wherewithal to destroy Boston if necessary, “notwithstanding the property and friends within it.” Since his arrival in Cambridge in late June 1775, the Virginian had been grimly determined to drive Sir William Howe’s redcoat regiments, over 9,000 strong, from the region and break the stalemate. With the eye of the surveyor and soldier, Washington soon grasped that emplacing batteries atop Dorchester Heights could put the British at his mercy.

The problem he faced in doing so was two-fold: where to come up with the heavy cannons necessary to pour metal upon the redocats, and how to take the heights before the British could respond with sea and land bombardments of exposed American troops approaching the hills or could seize the Heights before Washington.

On January 24, 1776, Henry Knox, a bold, portly bookseller and former Bostonian, solved the first problem. Having seized Fort Ticonderoga, in upstate New York, he and his men dragged the garrison’s ponderous cannons through dense snow and icy gusts all the way to Cambridge. Now, Washington turned his attention in earnest to Dorchester Heights.

The American commander’s counterpart, Howe, also had his sights on Dorchester Neck and the Heights. As The History of Dorchester notes,
“For a long time, the English officers had their attention fixed on what they denominated, on their plan, the twin hills, with the intention of fortifying them; but while they were awaiting reinforcements enough to hazard it, the good judgment of General Washington prompted him to secure the hills, and he improved the opportunity.”

In early March 1776, Washington and his staff rode out to Dorchester, and reined in at the farm of Captain John Homans, who lived in “the upper end of town.”

Because the “ground [was] so much frozen that earth could not be used, even had there been time for it,” for any potential forts, embrasures, and gun emplacements on the Heights, the Patriot commanders were combing the region for “fascines,” bundles of wood used to erect defenses. Homan’s acreage was full of white birch. Washington ordered a lieutenant and thirty men to cut down the birches and make the fascines. Then he sent out dispatches summoning “the citizens of this and the neighboring towns…to cart them [the fascines] on the night of the 4th, to the Heights.”

The ground upon which Washington intended to gamble his force was inhabited by “nine dwelling houses on the Neck, now South Boston.” Proof of the importance that the British attached to the Heights was Howe’s map that detailed each home’s location, as well as “the road and principal trees.”

The war was literally about to arrive at the front doors of those nine Dorchester households, those of “Mrs. Foster, Mr. Bird, Mr. Deluce, Mr. Williams, Mr. Farrington, Mr. Harrington, John Wiswall, Deacon Blake, and Oliver Wiswall.” Since Mrs. Foster’s home “was one of the best in the neighborhood…it was difficult to convince the continentallers [sic.] that it did not belong to a tory, as some of the rooms were even papered, which was considered very luxurious in those days. This house was the most westerly, and Dea. Blake’s the most easterly, of any on the peninsula, and these were both burnt by the British, who now had possession of Boston.”

On the night of March 4, 1776, as American cannons opened up on British positions in a gambit to divert Howe’s attention from the Patriots’ move against the Heights, reported teams of some 300 wagons and carts piled high with fascines creaked toward the slopes. So, too, did approximately 2,000 of Washington’s troops, cannons in tow, the entire procession snaking forward with as much silence as possible. Washington, anticipating that once his men climbed onto the Heights, the British would mount a bombardment and assault, had ordered the men moving through Dorchester to pack 2,000 bandages “prepared to dress the wounded.”

Many residents of Dorchester hauled timber toward the Heights on that icy, blustery night, chief among them “Mr. Boies.” The History of Dorchester records: “The late Mr. William Sumner, of Dorchester, so well remembered by many of those now living [in the 1850s], drove one team. He carried five loads before daylight, and remembered it with great satisfaction to his last days.”

With each step along the frozen track to the Heights, the men’s collective tension swelled: “No man was allowed to speak above a whisper, and thus the work went on silently, and unknown to the enemy, whose attention was in the mean time attracted elsewhere by a constant cannonading kept up from the American camp at Cambridge and in Roxbury.”

The troops went right to work on the hills’ summits, erecting gun emplacements and bastions with a “bird’s-eye” and deadly view of Boston and the water below. Once the Patriots had secured the position, they dug in mortars and large-bore cannons.

Howe, stunned to wake up on March 5 and find the Patriots on the high ground of the Heights, wrote to lord Dartmouth: “It [the capture of the Heights] must have been the employment of twelve thousand men.” Reportedly, the British general added: “The rebels have done more in one night than my whole army would have done in a month.”

As the Americans solidified their Dorchester perch, their labors did not come without a price. A group of soldiers who “were so imprudent as to build a fire for their comfort” gave British gunners a vivid target. The redcoat cannons erupted in “a severe fire upon them” from a battery at the corner of latter-day Washington and Dover Streets. Four Patriot soldiers and a surgeon named Dole died in the hail of shot.

On March 10, 1776, Abigail Adams wrote: “Sunday evening…A most terrible and incessant cannonade [against the Heights] from half after eight till six this morning. I hear we lost four men killed and some wounded in attempting to take the hill nearest the town, called Nook’s Hill.”

The Americans’ fortification of the Heights placed the redcoats in peril - and Howe knew it from the moment he first spied the “breastwork this morning [March 5th] …on Dorchester peninsula, which from its proximity had an entire command of Boston Neck and the south end of the town - a work which the king’s troops had most fearfully dreaded.”

Outmaneuvered by Washington and his “ragtag band” of Patriots, Howe had no choice but to abandon Boston. His nearly ten thousand recoats boarded the 125 transports and warships in Boston Harbor, with Washington’s guarantee that the British could leave unmolested if they did not burn Boston. When the victorious Americans entered Boston on March 17, 1776, the town had not been torched, but the redcoats had vandalized churches, homes, warehouses, and other structures.

The day of Boston’s liberation would become Evacuation Day - a date that would never have been possible unless the Patriots had taken and fortified Dorchester Heights.

Peter F. Stevens is the author of “The Rogue’s March: John Riley and the St. Patrick’s Battalion, 1846-48”; “Brassey’s”; and “Notorious and Notable New Englanders”; Down East Books. This article originally appeared in the Reporter in 2001.