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The Penobscot Fiasco

June 2024
15min read

It hardly seemed possible that a British garrison of seven hundred men could withstand a siege by the greatest American armada of the Revolution. But luck was not with the Americans that summer

“When the British came I was at Fox Island, with my uncle—where we went fishing in an open boat. We had news of their coming, and when the fleet came in sight, uncle said, ‘there comes the devils.’ We started for home and when the fleet followed us up we knew it was them.”

Thus did William Hutchings, a young fisherman trolling in the waters of Penobscot Bay, describe the first sighting of the British fleet. It was June, 1779, the Down East weather mild if moist, and the rebellion merely a distant stir. But the sudden appearance of those big ships, dim in the morning haze, signalled the coming of the Revolution to Maine and the beginning of a full-scale battle that American troops would wage with an equal mixture of fierce courage and almost unbelievable bungling.

Hutchings and his uncle paddled back to their hometown of Castine as the British ships rounded into the bay. The “devils” proceeded cautiously, aware that the region’s allegiance to the Crown was doubtful. They had been sent from Halifax with orders to establish an antiprivateering base and to support the local Tories, no easy job in an area where most of the natives were hostile or, at best, indifferent. The fleet—made up of troop transports and armed vessels, including three trim sloops of war—drew abreast of the steep promontory of Castine and fired a gun for pilots.

The rocky headland was a historic landfall, having been spotted by three pioneers of early North American exploration—Samuel de Champlain, John Smith, and James Rosier. The peninsula came into French hands in 1613 but changed flags at least five times in the course of the next hundred and fifty years, once even belonging briefly to their High Mightinesses—so the phrase went—the States-General of Holland.

But to the newly arrived British the peninsula still looked uncivilized, reconciled neither to man nor to his works. Their first landing appeared timorous enough to the townspeople who watched them disembark on the beach. Hatchings wrote that “the British … seemed as frightened as a flock of sheep, and kept looking around them as if they expected to be fired on by an enemy hid behind the trees.” They weren’t, but they nonetheless returned almost immediately to their ships and waited until the next day to establish a land garrison.

Brigadier General Francis McLean, in command of His Majesty’s forces—about seven hundred troops detached from the 74th and Sand infantry regiments—was not one to irritate the natives. He was urbane, just, decisive, and sufficiently aware of local folkways to know that those townsmen would behave themselves best who could profit most. If he were to win over the inhabitants of the town, the best way to start, it seemed, was to do something about their poverty. Despite its eventful seventeenth-century history Castine had been colonized for only eighteen years immediately preceding the arrival of the British, and few of the farmers and fishermen there had much put by. While there were Tory refugees like Dr. John Calef from Boston who lived better than their less fortunate neighbors, there was no spirited leadership to ignite native resentment into rebellion. Taking this into account, McLean issued a call for volunteers to work on a fort, emphasizing that the laborers would be paid and stressing the point that one purpose of the British presence was to protect the business of the “coast-fishing craft.”

The Tory Dr. Calef noted happily in his journal that some hundred townspeople turned out to work. Laboring alongside the British soldiers, they began to put together a square fort with a bastion in each corner. Work went slowly in the summer weather, and Hutchings noted that “the old General didn’t go about much, but the other officers used to. They went to Orland, to see old Vyle’s daughters.” By the end of July the fort consisted of a northern wall four feet high, low stone walls on the east and west sides, and no wall at all in the rear. It was so feeble a bastion that one soldier said he could “jump [over the walls] with a musket in each hand.” As yet no artillery had been mounted.

So the fort appeared to Lieutenant Colonel Paul Revere of the Continental Army as his transport headed toward Castine on the twenty-fifth of July. Through his telescope he could see most of the promontory and the primitive fort on the ridge above the town. It did not look particularly formidable.

The American force that Revere accompanied as chief artillerist was, on the other hand, impressive. News that the Penobscot expedition (as it came to be called) had left Boston had reached Castine a week before. British observers must have been aghast at the size of the force. There were nineteen armed vessels and twenty-four transports mounting among them 344 guns—the greatest exclusively American armada that would be gathered during the Revolution. The fleet, parading like so many cruising yachts into the bay, looked invincible.

The flotilla was commanded by Commodore Dudley Saltonstall of the Continental Navy, a man who had been in action at sea but had acquired no great naval reputation. His disposition, considered to be overbearing, prickly, and suspicious, was not improved by his knowledge that he had been the second choice for the job. The Massachusetts State Board of War, which had pulled together the expedition, had done well with the equipment (Saltonstall’s flagship, the frigate Warren , for example, had thirty-two guns—12- and 18-pounders); but in terms of men and organization things were not so good in the fourth year of an exhausting war. Four of the better-gunned ships were privateers, owned and commanded by gentlemen more interested in preserving their property than in obeying orders. And although the Massachusetts and Maine countryside had been scoured in an effort to meet the War Board’s call for fifteen hundred men, less than a thousand soldiers and marines ultimately sailed with the expedition.

Against this American armada the British had but three fighting ships- the sloops Nautilus , Albany , and North —and these they ranged across the mouth of the harbor. They had been retained from other duties by General McLean’s naval counterpart, Captain Henry Mowatt.

After surveying the situation from a distance Saltonstall raised flags and called the first of several conferences of his captains aboard the Warren . There was a strong wind blowing, and he seemed reluctant to attack. But eventually there was nothing for it: by 3:00 the wind had not diminished; if the deed was to be done that day, it must be then.

The battle began at the mouth of the harbor. Saltonstall sent in nine of his armed ships in squadrons of three, guns blazing. Under cover of their escorts’ fire the American transports were brought close inshore where the cliffs at the harbor entrance leave off and the shore rises more gradually.

But a combination of poor shiphandling and British gunfire thwarted the attack. According to Revere’s terse account of the action, “A number of men attmpt to land under Brigar Wadsworth; they approach, orders are given for them to return; the enemy fired upon them, and kill one Indian.”

Militia Colonel Josiah Brewer, a friendly observer of this frustrated assault, had a brother with the Penobscot expedition. He met with him that night, and early the next day the two men went aboard the commander’s flagship. Colonel Brewer gave a full and precise description of the British fort, with discouraging results. “I then told the Commodore that being all the force he would have to meet, I thought that as the wind breezed up he might go in with his shipping, silence the two vessels [ sic ] and the six-gun battery, and land the troops under the cover of his own guns, and in half an hour make everything his own. In reply to which he hove up his long chin, and said, ‘You seem to be d—n knowing about the matter! I am not going to risk my shipping in that d—n hole!’” And so the day wore on with the same luckless landing attempts as the day before.


The leaders of the army forces, however, were not so cautious as SaItonstall. Brigadier General Solomon Lovell was a man of undaunted courage, although he had never commanded troops under fire. Most of his men were similarly untried, so rawly pressed into service that they had paraded together only once. His second-in-command, General Peleg Wadsworth, was a tested and imaginative soldier.

That night, the night of July 26, Wadsworth succeeded in throwing ashore two hundred men, twenty marines, and four 4-pounders on Nautilus Island, across the harbor from the town. The Americans took a small British force there and, despite foul weather, managed by late evening to get some heavier guns ashore. They hauled them up to high ground, where their presence forced the British sloops to move upriver. The night following this minor victory Wadsworth and Lovell planned an audacious assault that deserves to be remembered as one of the Revolution’s most gallant actions.

At three o’clock on the morning of July 28 a combined force of two hundred marines and two hundred militia prepared to move in toward the heights on the western or bay side of the peninsula. The brigs Hazard and Sally and the majestically named Tyrannicide laid down a barrage, firing round after round at the foggy shore. The men piled into their small boats and rowed desperately through the noise and smoke. Even before they saw the foaming beach, they heard the sound of musketry from the high, black pines that loomed out of the crags. The bullets pelted down around the boats as they drew up, slick with salt spray, on the cold, kelp-hung rocks. The men scrambled for what scant cover they could find and peered up at the heights they would have to scale.

Officers ran back and forth through the ranks shouting orders, rallied the nervous men, and split them into three parties. The party in the center stayed where it was in order to keep up a covering fire on the British in hopes of taking some pressure off the two flanking parties. As they began to load and fire up the noisy slopes the flanking parties blundered off along the natural wall that edged the beach.

On the right a squad or two of frightened, exhausted militiamen made their way up steep, rocky ground in the teeth of stiff musketry and came at last to a British battery. They routed the astonished defenders and seized the guns intact. On the left marines had to contend with an almost sheer rock face some forty feet high. Gasping and cursing, they made their way up to the crest, where they found steep but passable ground and galling gunfire. Facing them were troops under a seventeen-year-old lieutenant named John Moore, who would become famous as a general in the peninsula campaign of 1806. But luck was not with Moore that morning, and he was forced to draw back his troops in the face of the onslaught of Americans.

Now the Americans had pushed the British back all along the line. They had paid a high price for it; Lovell reported losing fifty men in the halfhour action. Four hundred colonials had overcome a seemingly unassailable position defended by a nearly equal number of seasoned British troops. Yet the glory of that brief fight would not save the expedition.

Immediately the few hundred Americans who had gained the heights came under the guns of the British fort, where seven hundred enemy soldiers were waiting for them. These men, however, were by no means confident. The walls of the fort were about waist-high and seemed from the inside to offer little protection against a determined assault. In fact General McLean, remarking that he had won nineteen battles but expected to lose the twentieth, stood with the pennant halyard in his hands, ready to strike the colors as soon as the attack came on. Later he scoffed at his adversaries: “I believe the [American] commanders were a pack of cowards or they would have taken me. I was in no situation to defend myself, I only meant to give them one or two guns, so as not to be called a coward, and then have struck my colors … as I did not wish to throw away the lives of my men for nothing.”

But the fort seemed far more potent to those on the outside. Paul Revere wrote of it: “I had a fair view of the Enemy’s Fort with a good Glass; I could see that it was as high as a man’s chin; that it was built of squared logs; was Abbeteed; that they had begun to Fraise it round the rampart; that they had two guns mounted which they fired in Barbet.”

There is no record of the Americans’ battle plan after the assault on the heights. But after a conference on the twenty-ninth a report was dispatched to Boston stating that the peninsula could not be taken unless more men were immediately forthcoming. This urgent message was sent by whaleboat, perhaps the slowest and least secure means available. The Americans then settled down to wait, failing to understand that time was not on their side; each day the British made the fort stronger.

The expedition’s leaders also made a few haphazard efforts to get control of Castine Harbor, which they correctly viewed as the key to the whole operation. Their reasoning went thus: if the guns of Mowatt’s ships could be silenced, and if Commodore Saltonstall could be persuaded that it was safe to enter, then the American fleet with its superior firepower could finally be put in a position where it could do some good.

Thus, as the weather turned benign, the Americans busied themselves erecting batteries on the periphery of the British position. They moved cautiously among the islands and bits of mainland that form the eastern shore of the harbor, floating their cannon on gondolas; they found a particularly good location for a battery on the mainland that forms the harbor’s northern shore. And all the while the men on the heights moved their zigzag line of entrenchments in closer to the fort—until they were only seven hundred yards away.

There was reason to believe the plan of encirclement might work. Captain Mowatt had been sufficiently bothered by the American battery on Nautilus Island to withdraw his ships to where they were within range of the new mainland battery. Young Hutchings considered the bombardment of the British ships from that position hugely successful. His father was one of the few militant patriots then living near Castine who had risked everything to support the expedition, and the boy himself was assigned to help build and arm the new battery. His recollections show that he took particular delight in the summertime war: “We kept up a hot fire on the ships, and drove the men ashore and below. There were three frigates [ sic ]—the Albany , North and Nautilus . We could hear our shots go— thud —into them. We cut away an anchor hanging at the bows of one of them. I marked where it fell, as I thought some time or other I might want to get it up.”

But Commodore Saltonstall refused to be convinced that the harbor was secure enough for him to come in. He preferred to conduct impressive-looking naval exercises in the bay with the many guns of his vessels eloquently silent. Was he a coward? Had he taken British gold? The questions would be asked later at his court-martial.

His fear of the British cannon in the fort and on Mowatt’s ships—if indeed that is what held him back—was not justifiable. Three years later, when the British were even more firmly in possession of Castine and the fort better armed, a single American demonstrated what a good sailor could do in that harbor. The man was Captain George Little of the sloop of war Winthrop , who had originally been offered command of the Penobscot expedition. Some time in the year 1782 Little found himself pursuing a large British brig along the coast. He was unable to bring her to an engagement, and eventually the enemy ship eluded him. From another ship overtaken in the bay he then learned the brig’s location: in the middle of Castine’s welldefended harbor. Knowing that a daytime attack would be folly, Little planned to enter at night and dressed his men in white to distinguish friend from foe. He glided into the harbor with the wind behind him after sunset on the turn of the tide.

The brig’s officers apparently felt secure beneath the guns of the fort. They assumed that the swiftly oncoming sloop was a prize sent in by a British squadron. “You will run aboard,” they ordered. Little, taking his cue well, answered, “I am coming aboard,” and dispatched a platoon of men under Lieutenant Edward Preble, the same Preble who is known for his later service with Decatur in the Barbary States. Preble sprang aboard the brig with fourteen men, but the rest missed their chance as the sloop sped past. Little called after him, “Will you have more men?” The undaunted Preble replied, “No! We have more than we want, we stand in each other’s way.”

Most of the British crew leaped overboard, and Preble captured the remainder without difficulty. He raised sail on the brig as fast as possible to follow Little in the sloop out of the harbor, whose shores were lined with curious townsfolk. On his way out he had to make three tacks and came under heavy fire from the fort. But he made it—though later reports said that he and Little (both of whom reached Boston safely) could pick spent bullets off their decks by the bucketful.

But Commodore Saltonstall was no Little. In the two weeks following the attack on the heights his fleet had accomplished nothing, and the attempts to strangle the British by getting command of the harbor had also failed. The expedition’s army officers sent a deputation to the commodore requesting more effective action; even his fellow naval officers called for more decisive measures. Then, as if to set him an example, on the afternoon of August 11 two hundred of General Lovell’s men staged a fierce attack on the fort that was broken off only after severe losses.

That same day a strong letter from General Lovell arrived aboard the flagship. It began, “Sir: In this alarming posture of affairs, I am once more obliged to request the most speedy service in your department.” The letter went on to describe the army’s straitened position and to repeat an ominous rumor: a British fleet was on its way. Lovell continued: “My situation is confined; and while the Enemy’s ships are safe, the operations of the army cannot possibly be extended an inch beyond the present limits; the alternative now remains, to destroy the ships, or raise the siege … not a moment is to be lost; we must determine instantly, or it may be productive of disgrace, loss of ships and men; as to the troops, their retreat is secure, although I would die to save the necessity of it.”

The letter concluded with words that might have been written as the expedition’s epitaph: “I feel for the honor of America, in an expedition which a nobler exertion had long before this crowned with success. …”

Even with the urgency of Lovell’s letter the Americans still needed two days to achieve a coordinated plan for the final land and sea effort. After a last-minute army council on the foggy morning of August 13 (when the vote on whether the siege should be abandoned was a close ten for withdrawing, fourteen for staying) General Lovell set out from his line with another battalion of two hundred men. If his attack had any plan, it was apparently the desperate one of drawing the British out from the fort and overcoming them. Then Saltonstall might deign to come in.

As expected, the British gunners opened up with grapeshot and stayed behind the fort’s ramparts. They were convinced that this was the full enemy attack, and they were ready for it. Paul Revere, scurrying to bring his artillery to Lovell’s assistance, advanced with the rest of the little battalion through the thinning fog. They reached the town and kept up the hill toward the British, severing the vital line between Mowatt’s ships and the fort.

How close to the fort they came and how near they were to carrying the day is not known. But we do have Revere’s report. Standing high up on the peninsula’s slope as the sun went down on the other side, he strained through the smoke and haze to see what their efforts had won. “The Enemy fire grape at him [Lovell], but do not come out. Our Ships get under sail, we supposing they were coming in, when to our great mortification, (the Fog clearing away) we see five sail of ships in the Bay.” There was no doubt whose ships they were; the only question was how many more British sail were yet to come. Revere and Lovell saw their situation for what it was: hopeless. “It being near sundown & a shower coming on, the General led off his men.”

Sir George Collier and his British relief squadron had indeed arrived in Penobscot Bay and were now clearly visible from Castine. The ships numbered seven, rather than five, with a promise of more over the horizon. Their firepower and complements were awesome—a total of 204 guns and 1,530 men—even without counting the Nautilus , Albany , and North . The American fleet, for all its armed might (a total of 344 guns), was nothing but a state navy with highly independent ancillaries, the whole under a weak Continental command.

The next morning, most of the shore guns and troops having been removed to their ships during the night, Saltonstall’s fleet of warships and transports moved to the mouth of the harbor. The Americans, surging slowly in the swell, formed a crescent as best they could—the fighting ships placed to meet the enemy first in hopes that the transports might slip past to freedom.

The British, with their taller spars and greater sail, seemed to have no difficulty maneuvering. Undeterred by the rebel crescent, they came on, sailing directly at the center of the American force. Then, turning his ships in passing, Collier fired successive broadsides. The Americans, without a council and without a signal being raised, unanimously determined on flight.

There was perhaps as much prudence as cowardice in the decision. By fleeing up the Penobscot with reliable native pilots the Americans had, at any rate, a chance to debark their troops and get other supplies off before destroying their ships—most of which had been regarded by their owner-skippers as too valuable to risk in the preceding days’ combat. If they had chosen to fight or to run to sea, they might have saved nothing.


As it was, the fleeing ships presented a panorama of disaster. Lovell wrote in his journal: “It would be a fit subject for some masterly hand to describe it in its true colors;—to see four [in fact seven] ships pursuing seventeen sail of armed vessels, nine of which were stout ships—transports on fire—men of war [having wrecked themselves] blowing up … every kind of stores on shore … throwing about, and as much confusion as can possibly be conceived.”

The Penobscot expedition, despite the incidents of American heroism, ended as a crushing British victory, one in which a superb army and navy defeated at every level the efforts of local forces to oppose them. Three sloops of war and a small body of troops had withstood a twenty-oneday siege against a fleet and army six times their strength. The Massachusetts state navy was obliterated; the Continental Navy itself, deprived of vital support, was eclipsed for the remainder of the war. Massachusetts’ indebtedness was so great that she was unable thenceforth to raise a levy or equip a sizable body of fighting men.

Lovell’s proud army, now split into bands of starving fugitives, fled south and west through the Maine forest. A few hundred survivors of the expedition trudged wearily across the causeway into Boston two months later, at harvest time; the debacle had claimed over five hundred American lives.

The first item of business for those who returned was to fix the blame for the expedition’s failure. A brawling public battle of recrimination began that did further damage to the Continental Navy and Army. Among other expedition leaders Paul Revere was court-martialled. “Disappointment as usual wrought injustice,” he wrote, “and censure undeserved fell on many who did all that under the circumstances could have been expected.” But his convincingly detailed story of how he had made do with the few guns at his disposal brought him an eventual acquittal. The records of Commodore Saltonstall’s court-martial have, unfortunately, been lost. But the rumor that he had been bribed was apparently snuffed. All that remained was the certainty that to win the long, far-ranging rebellion that stretched on ahead of them Americans would need better men and less vainglorious strategies.

Castine stayed in British hands until long after the official end of the war, but eventually Dr. Calef and his Tory friends had to withdraw to Halifax, the last of so many Maine summers having come to an end.


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