Attack up the Connecticut River: The First British Raid on Essex

War at Sea and Waterways (1775–1783)

April 14, 2020
by Matthew Reardon Also by this Author


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By April 1782, the war in America was supposed to be over. It had been nearly six months since Lord Cornwallis surrendered his army to Generals Washington and Rochambeau at Yorktown. The previous February, the British Parliament had voted to stop funding the war. Peace negotiations between British and American representatives had begun in Paris. But almost 4,000 miles away, along the Connecticut coastline, the war continued unabated.

For the previous six years, the Connecticut militia had been engaged constantly with the Associated Loyalists and their counterparts, the Loyal Refugees, based on British-occupied Long Island.[1] These loyalists were irregular forces which operated independently of the regular British army in New York City. Their ranks were made up of displaced New England loyalists, many of whom were from Connecticut. They armed and equipped themselves and even had their own small naval vessels. Starting in 1776, the two sides routinely launched raids against each other’s coastal towns in fighting which came to be known as the “Whaleboat Wars.”

Early in the first week of April 1782, the Refugees did something they had not done before: they proceeded into and then up the Connecticut River. Up until then, they had never ventured very far from the coastline.[2] This attack would have been completely lost to history had it not been for a brief mention in two local newspapers and a single letter found in the Governor Jonathan Trumbull Papers at the Connecticut State Library. The letter to the governor was drafted by the three selectmen of Saybrook: Samuel Field, Richard Dickinson, and William Hart Jr., on April 26, 1782. Its main purpose was in response to the raid, to lobby the governor for additional resources which could be used to more adequately protect their coastline as well as the lower part of the Connecticut River.[3]

Saybrook was a coastal town just over thirty miles east of New Haven, which traced its history back to the seventeenth century. Today, the oldest part of the town is known as Old Saybrook. In 1782, the town was much larger and also included the modern-day towns of Westbrook, Deep River, Chester, and Essex. During the Revolutionary War, two of the town’s boundaries ran along the waterfront. The southern boundary rested on Long Island Sound, while the eastern boundary ran along the Connecticut River. An earthen fort, equipped with six guns, garrisoned by a small company of state troops, protected the mouth of the river. The fort, erected at Saybrook Point, stood at the western entrance of the river, a few miles east of the main part of town.[4] The garrison, under the command of Lt. Martin Kirtland, was responsible for not only the protection of the fort, but also for patrolling the adjacent coastline and riverfront in order to counter the illicit trade. In 1782, the company was understrength and “wholley destitute” and not entirely prepared to resist any attack, much less a raid up the river. The armed boat Success, which was normally assigned to support the fort, was not even present. It was off on a mission in Sag Harbor.[5]

Detail from a 1780 map of Connecticut showing Saybrook (Saijbrook) at the center along the Connecticut River where it enters the Long Island Sound. Lyme (Lijme) is across the river, while New Haven is to the far left. Pettipaug (Putty Pogue) is north of Saybrook along the river. (New York Public Library)

Writing to the governor, the three selectmen told Trumbull, “Two [to three] Refugee Boats . . . made an Entrance into Connecticut River in the Night Season” and slipped by the Saybrook fort as well as Kirtland’s guards. These two or three boats were likely whaleboats which the Refugees typically utilized. Whaleboats were crewed usually by seven to ten men each, and were open row boats, generally about thirty feet long, equipped with a single mast. The crews were typically armed with swords or firearms, though armament varied from boat to boat. Some were unarmed, relying solely on the weapons carried by the crews, others were equipped with small light cannon and/or swivel guns.[6]

At most, with two or three boats, the total attacking force of Refugees probably only consisted of twenty to thirty men. This low number assuredly meant that this was not meant to be a large-scale attack. This was typical of all their attacks. They were supposed to get in, acquire all they could, and then make it back to their boats offshore or back to their base on Long Island. That night, the Refugees, according to the selectman, “Penetrated as far up the River as Eight Miles,” placing the point of attack at the village of Pettipaug, which is present-day Essex. This is also supported by the newspaper reports.[7]

Pettipaug was not an entirely random target. Without further information we are left to guess the objective of the raid, but it more than likely had to do with shipping. This is the same reason the British attacked the town three decades later during the War of 1812.[8] With its close proximity to the river, the coves around Pettipaug were home to several shipyards that constructed a number of smaller vessels including packets, sloops, schooners, and brigs. Some were privateers, others were merchant ships. The merchant trade was very active up and down the river throughout the war. Connecticut’s first warship, the 20-gun brig Oliver Cromwell, was built at Uriah Hayden’s shipyard in 1776.[9]

Under the cover of darkness, the Refugees proceeded towards the Connecticut coastline and then into the Connecticut River completely undetected by Kirtland’s guards. As they proceeded upriver, they remained undetected. As they neared Pettipaug, they encountered, captured, and then subsequently, according to the selectmen, “Plundered three vessels.” These vessels were, apparently, lightly guarded and were easily overwhelmed by the armed Refugees. The attack was done so quietly that it did not arouse the local citizens, nor did it result in calling out the militia.[10]

After capturing the vessels, the Refugees did not land in Pettipaug or even approach the village. According to the selectmen’s letter, a detachment may have continued upriver for about another two miles until they reached Brockway Island, a short distance south of the present-day town of Deep River. But the majority of the attacking force did not venture far from Pettipaug. Sometime between 4:00 A.M. and 5:00 A.M, they turned around and headed back down river. According to the selectmen, on their return, the Refugees carried with them the three captured vessels along with two other vessels they picked up along the way.[11]

But as morning approached, the situation started to slightly worsen for the Refugees. At around 6:00 A.M., the same time the Refugee flotilla was passing the ferry crossing site between Saybrook and Lyme, nearly two miles north of Long Island Sound, the sun began to rise. Their cover was gone. The wind, as well as the river tide, were judged to be too low. This was further complicated by river itself. At this point, the river has a deceptively narrow channel, with lots of sand bars and drifts. Under the present conditions, it would be difficult and dangerous to attempt to take off the larger captured vessels. So, it was decided that the larger vessels, along with the prisoners taken aboard them, had to be left behind. Before leaving the vessels, according to the Gazette, the Refugees “nail[ed] down the [prisoners] in the cabbin.”[12]

It was probably at this time the Refugees took possession of the “Ferry-Boat and one or two other Boats,” said the Gazette. These would have an easier time navigating the river than the larger vessels. Determined to gain something by the raid, the ferry boat and other smaller boats were also presumably loaded by the Refugees with the plunder taken from the larger vessels.[13]

Once the prisoners were secured and tradeoff completed, the Refugee flotilla continued onward down the Connecticut River. Repassing the Saybrook Fort, they avoided any confrontation with either Kirtland’s guards or any other militia. From there, they escaped out of the river and into the Sound and then eventually safely back to their either their own vessel or vessels waiting offshore or their base on Long Island.[14]

The raid on Pettipaug was in all respects a British success, albeit a minor one that had no real effect on the war. Never before during the war had the Refugees been able to penetrate so far into the state. Not only that, but in doing so, they completely evaded the state troops, the militia, and local citizens. Weaknesses in the state’s defenses were definitely noted. Casualties were presumably either few or non-existent. While they were not able to take the larger vessels, they took some things with them. The Gazette described the captured vessels as a ferry boat and one or two small boats, while the selectman claimed they took two, unidentified, vessels with an untold amount of goods. The two vessels mentioned by the selectmen were probably the smaller boats mentioned by the Gazette, implying that the goods taken were loaded on the ferry boat as well as the smaller boats. Had it not been for the wind and tide conditions, at least two more larger vessels, with prisoners, would have assuredly been taken as well.[15]

The success of the raid assuredly embarrassed the militia, the state troops and local government leaders. This was especially true in Saybrook and the reason the letter was sent to the governor. But at least, according to the selectman, it was not the fault of the garrison at the Saybrook Fort. “Our Small Guards,” they explained, “in their Situation, were unable to afford any Relief to the Sufferers.”[16]

Before drafting the letter to Trumbull, the selectmen had sat down with each other and discussed their best options. At least two of them, William Hart Jr. and Richard Dickinson, were involved in the sea trade and had strong personal interests in protecting the Connecticut River, which they called the “Key to the State.” They reminded the governor that if the mouth of the river was not protected, the trade which operated in it “must greatly suffer.” At least one, Hart, was a militia officer, and had seen some active service.[17]

In the letter, the three selectmen, first and foremost, asked for additional funding. They complained that due to lack of funding from the state, they were not able to enlist enough troops into Kirtland’s company. The town had funded most of the unit themselves and were already stretched financially thin. This was due in part to—and they made specific mention of it—the heavy “Public Tax” the General Assembly had levied on them and the rest of the state. They also begged the governor to order militia from the interior part of the state to Saybrook. Once there, they could better defend the fort as well as allow Kirtland to post more guards along both Long Island Sound and the Connecticut River. The selectmen also recommended they be provided with a six-gun vessel and two additional whaleboats which could support the garrison by patrolling the river and the Sound. They closed the letter by telling the governor that unless supported, if the enemy renewed their attack they could not effectively hold the town and would be forced to evacuate it.[18]

Unfortunately, lacking any further documentation, we do not know how seriously Governor Trumbull, his Council of Safety or the General Assembly took the selectmen’s recommendations or if any of them were ever put into action. If they were not, this, sadly, would not have been uncommon. Even other places in the state deemed more strategically important than Saybrook, like New London, which were also constantly asking for more resources and funding, received little or none. To make matters worse, by 1781, the state was effectively bankrupt and could barely afford to pay its own soldiers serving in the Continental Army.[19]

The only documented support sent to the garrison at Saybrook was a barrel of gunpowder which was not ordered there until the following June. In all likelihood, the garrison and town of Saybrook received no additional support from the state. They were forced to make do.[20]

Fortunately for them, no attack came. Except for a small skirmish at East Guilford, modern-day Madison, about fifteen miles to the west the following month, attacks along the coastline of Connecticut, which had gone on regularly for the better part of six years, ceased. This followed the controversial execution of an American prisoner by members of the Associated Loyalists. As a result, the British commander-in-chief, Sir Guy Carleton, ordered the Associated Loyalists to be disbanded. This alone put an end to the attacks on Connecticut. Despite this, a garrison was kept at the Saybrook Fort for the duration of the war. The fort would not be tested again until the War of 1812 when the British launched their second and most devastating attack on Pettipaug.[21]


[1]Though the two were separate organizations, most American reports and correspondence refer to them only as the Refugees.

[2]Connecticut Gazette, April 5, 1782. The exact date of the attack is not known, nor was it given, but the Connecticut Gazette stated the attack occurred “a few nights ago,” placing the raid on April 1, 2 or 3.

[3]Selectmen of Saybrook to Governor Jonathan Trumbull, April 26, 1782, Governor Trumbull Papers, 16:103a-b, Connecticut State Library.

[4]Louis F. Middlebrook, History of Maritime Connecticut During the American Revolution (Salem, Massachusetts: The Essex Institute, 1929), 15. Capt. Adam Shapley to Governor Jonathan Trumbull, July 4, 1781, Governor Trumbull Papers, 14:323b-d, Connecticut State Library. A fort stood on the site since the Pequot War, but has long since vanished. The site of the fort today is not the one that is “recreated.” Rather, it was closer to the waterfront, probably on the site of today’s Saybrook Point Marina and Resort. Only one company return is known to exist prior to the attack. It was taken upon a review of the company in July 1781. At that time, it mustered one lieutenant, three sergeants, and thirty-seven rank and file. But as it was noted, the “men are but very indifferently provided with Ammunition.” The guards were considered “State Troops,” members of the militia who agreed to serve for a set amount of time, usually six to eight months, under officers appointed by the General Assembly.

[5]Selectmen of Saybrook to Governor Trumbull, April 26, 1782; Middlebrook, History of Maritime Connecticut, 230. In August 1781, ten members of the company were detached and sent to New London which was deemed more strategically important. Most became casualties in the subsequent British attack on New London.

[6]Selectmen of Saybrook to Governor Trumbull, April 26, 1782; Connecticut Gazette, April 5, 1782.

[7]Selectmen of Saybrook to Governor Trumbull, April 26, 1782; Connecticut Gazette, April 5, 1782. While the selectmen placed their farthest penetration point as eight miles upriver, the Gazetteplaced it only at six miles. Even with the discrepancies, both distances place the attack in the vicinity of Pettipaug.

[8]For more information related to this attack, see Jerry Roberts, The British Raid on Essex: The Forgotten Battle of the War of 1812 (Middletown, CT: Wesleyan University Press, 2014). The two raids bear a lot of similarities.

[9]The Oliver Cromwell was captured by the Daphne in June 1779 off Sandy Hook, New Jersey.

[10]Selectmen of Saybrook to Governor Jonathan Trumbull, April 26, 1782.


[12]Ibid.; Connecticut Gazette, April 5, 1782. Special thanks to my friend and naval historian Daniel Walls for helping me better understand these features of the Connecticut River.

[13]Ibid. There was really no other reason to take the ferry boat other than to convert it into a supply barge. It would not prove useful or valuable in future coastal attacks.

[14]Connecticut Journal, May 23, 1782. During such attacks, the Refugees were usually escorted or assisted by larger naval vessels that operated under their control. They probably had at least one awaiting their return to Long Island Sound, but none of the American sources mentioned them. Prior to their attack on nearby East Guilford, present day Madison, the Refugees were seen patrolling Long Island Sound and attacking merchant vessels with two brigs, a sloop and a galley.

[15]Connecticut Gazette, April 5, 1782.

[16]Selectmen of Saybrook to Governor Jonathan Trumbull, April 26, 1782.

[17]Ibid. Hart served as major and commanded the 1st Regiment of Light Horse, a mounted militia unit. The regiment saw action during the Danbury Alarm in the spring of 1777.


[19]Richard Buel Jr., Dear Liberty: Connecticut’s Mobilization for the Revolutionary War(Middletown, CT: Wesleyan University, 1980), 239-281.

[20]Leonard Woods Labaree, The Public Records of the State of Connecticut For the Year 1782 with The Journal of The Council of Safety From January 17, 1782, to December 16, 1782, Inclusive (New Haven, CT: Quinnipiack Press, Inc., 1942), 4: 254.

[21]Connecticut Journal, May 30, 1782.

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