General Washington's Spies on Long Island and in New York

“On the 18th, by a courier from the east end of Long Island, the first intelligence was received of the arrival, on the 10th, of the French off Rhode-Island, which I transmitted immediately to Admiral Arbuthnot.

“In the hope that I might yet be in time to undertake something offensive against the enemy, either by a land attack solely, or, if the Admiral should have found it advisable, a joint attempt with the fleet, I determined as speedily as possible to put a body of troops afloat in the Sound, ready for operation to the eastward, if further information should warrant it, and not too distant to return rapidly, and act against the rebel army, should they, in my absence, form an enterprize against these posts.

“Many causes conspired to retard the arrival of transports at Frog’s-neck, from which place my embarkation was only effected the 27th. During this time all hopes of success from a coup de main were of course wafted away.

“The Camilla and Amphitrite, which were appointed to convey us, joining the same day, I proceeded with the transports to Huntington-bay, where I was honoured with such accounts from the Admiral of the attention the enemy had given to fortify themselves, that I no longer entertained an idea of making any attempt solely with the troops. I cannot judge what might have been expected from a joint operation; but I presume that, in the aspect affairs bore at that time, it was not to be undertaken with propriety.

“On the 31st therefore I returned to White-stone, where I disembarked the troops, keeping the transports in readiness to receive them again, if necessary; and the army encamped near the shore.

“During this time, Washington, by a rapid movement, had, with an army increased to 12,000 men, passed the North-river, and was moving towards King’s-bridge, when he must have learned that my armament had not proceeded to Rhode-Island. He (I apprehend in consequence of this) re-crossed the river, and is now near Orange Town.

“The Admiral is near Gardiner’s-Island, to which place I shall, if possible, proceed to confer with him and his Officers.”[23]

General Washington now ordered a chain of Dragoons to be posted between New London and Headquarters. There were to be 3 every 15 miles apart, to convey messages from the Culpers and the French Fleet. Colonel Sheldon complied under protest, as his letter following shows:

... “I have this morning early sent off an officer with a sufficient number of my most trusty Dragoons to post them at every fifteen miles distance, or as near that as the necessity of forage would admit. The officer is instructed to move on the Dragoons to Tower Hill, if Mr. Shaw cannot furnish the expresses beyond New London. The stages at which the officer is ordered to post the Dragoons, are as follows: Beginning at the Eastward, namely New London, Lyme, Guilford, New Haven, Stratford, Green Farms, and Stamford. I do not post another party between Stamford and Head Quarters lest the plunderers from below, which infest the intermediate country should take off the men or seize on the Dispatches when they should arrive.

“While I with the utmost cheerfulness and alacrity obey your Excellency’s orders I cannot but regret the necessity of detaching so many of my Dragoons from the field. I do not mention this as if your Excellency had not considered the expense of furniture and equipment of Dragoons, but to beg for the Honour of the Regiment and the good of the service, your Excellency would be pleased to excuse them from this duty as soon as possible.

“Elisha Sheldon.”

“Sir, Your several dates of the 23d and 26th of July came to hand on the 4th inst, and observe the contents. Being still in a feble state (but mending) was obliged again to have recourse to Austin Roe, and dispatched him the same evening with such directions as thought proper. He this instant returned with the enclosed from Culper, Junior. I hope it contains all the needful. Roe hath no verbal account worthy of notice. Also you have enclosed the state of the Garrison at Lloyd’s Neck, but it is not satisfactory to me, but is the best that could be procured this time. Coll. Simcoe with his regiment of Rangers, and three companies of Queens County Militia Foot, and about thirty of Coll. Ludlow’s Regiment, have been for some time past in the County, the main body at Southampton, some at the River Head, some at South Mills, about 30 at Coram. What they have come down here for is unknown.

“I purpose to go to 727 for the benefit of our 115, and have 130 ready for you, em. Also have the promise of the exact state of Lloyd’s Neck, which shall then transmit. Am in great haste and in the interium am Your Sincerely,

“Saml. Culper.”

An interesting letter followed Woodhull’s visit to New York, which is dated August 16, 1780, and reads as follows:

“Sir, I have this day returned from New York and am happy to inform you that Culper Junior hath engaged to serve as heretofore. I have nothing to enclose from him to you, as there’s not a word of intelligence worthy of notice in New York. I have the satisfaction to assure you that the judicious Torys in New York are more dejected now than ever I knew before, on account of the neutrality entered into by the Powers of Europe. A few victualling ships were to sail yesterday to the fleet now laying in Gardiner’s Bay. Clinton, with about 7000 men are cantoned from Whitestone to Jamaica for this ten days past have been ordered to hold themselves in readiness together with the fleet that still lays at Whitestone. Common reports say they are about to proceed to Rhode Island, but it is very uncertain. No person can tell, but, by all means be upon your guard. There is in this county the Queens Rangers, three companies of Queens County Militia Troop, Coll. Fanning’s Regiment, the 17th Dragoons, German Huzzars, all marching to the Eastward, also three Regiments more were ordered to march recently. Say they are to embark at the east end of this Island. We have a report that the second division of French hath arrived. Hope it may be true. Tryon, Patterson and Mathews are about to sail immediately in the packet for Europe. The person I depended upon to procure a very accurate account of Lloyd’s Neck, is taken very ill and hath put it out of my power to forward it now. I have ordered 725 to return here again on the f i instant, and intend to send you as frequent dispatches as possible as long as things are in such motion. In the interim wishing you health and prosperity I am &c.

“S. Culper.

“N.B. Next opportunity you’ll have the papers regular as heretofore. Should have sent them now but lost them out of my pocket on the road.

“I forgot to mention that General Clinton in person was escourted through this Town yesterday by the mounted Rangers, 17th Dragoons, and German Huzzars, in all about two hundred and forty horse.”

The hazard of their employment is calmly illustrated in the next letter addressed to Major Tallmadge: It was necessary for them to kill a man whilst waiting for Culper’s messages. Brewster writes:

Through Major Tallmadge General Washington answered the above from Headquarters at Orange Town, August 21, 1780, as follows:

Dear Sir. I recd. yours of yesterday morning last evening. It is unfortunate that Lt. B—— could not bring off C—— Junr’s dispatches, as I imagine they were of consequence. You will therefore endeavour to procure them as soon as possible.

I have information from another quarter, that Sir Henry Clinton had gone towards the East end of Long Island, and that the troops at Whitestone are again embarking. Should the last piece of intelligence reach you, well authenticated, you will be pleased to transmit it immediately to Genl. Heath at Newport, as well as to me, as you will always do anything which seems to interest the French Army and Navy.

If there are any other Continental Crews upon the Sound besides those under Lt. Brewster’s directions, they are there without my knowledge. You will therefore desire him in my name to take what hands he wants from them, and to report who the others are and what business they are upon. I am Dear Sir, yr. most obt. Sert.

Go: Washington.

Brewster was roused to action. Therefore without waiting to hear from the General or Major he again crossed to Long Island, as his letter following shows:

Fairfield, Aug. 21, 1780.

Dear Sir. I this morning came from the Island. I got three boats last Saturday night and went over in search of Glover and Hoyght, but could hear nothing of them. They never stayed to bury their dead man. They carried another away with them mortally wounded. Setauket is full of troops. It is thought they are going eastward. Austin came to me yesterday and told me I had best not come on till the middle of next week as the troops is so thick in Town and marching eastward. I wrote to you the eighteenth instant which I expect has come to hand. Skinner is so he will be able to do duty soon as he will be wanted. I heard nothing from Culper this time. I should been back the next time had not the wind been so high. There was a small fleet of large ships went to the Westward this morning. Capt. Jarvis supplied me with men this time to cross. I shall want one man to make up my crew for one boat and should be exceeding glad of five more to man the other boat for the cussed refugees are so thick I cant go amiss of them....

C. Brewster.

As soon as Brewster had delivered the above message he crossed to the Island again. His next letter follows:

Fairfield, August 27th, 1780.

Dear Sir: I returned this morning from the Island. I crossed on 22d. inst. and was detained by Culper until last night. I did not see Culper, he is sick. He did not appoint any time for me that I know of. It was with great difficulty that I got the dispatches. The troops are very thick. They are at Miller’s Place, and Coram, Setauket and the Branch, and are like to stay some time, and the Refugee boats are with them. Glover and Hoyt has been to Drowned Meadow and disarmed them all, on Friday last, and I was obliged to lie still for the want of another boats crew. There is a fine boat at Stanford that rows with eight oars that belongs to the public, under Capt. John Suttin, with a crew of Continental Soldiers that was ordered by General Howe, and I believe that Jubis Fish has one or two boats at Horse Neck, but I am not certain what public property and Continental Soldiers. This is a fine time to take some of the Officers. They are out with their hounds every day. I lay up back of Esqr. Strongs yesterday and there came a Lieutenant of 17th Regiment within gun shot of us, looking for Esqr. Strong’s hounds afoot, but he begged so hard I thought it not best to take him as it was so near his house. They are riding continually from one staghorn to the other. The troops are all come from the Eastward, as far as Miller’s Place. Sir Henry Clinton gone to New York and the British fleet has sailed from Gardiner’s Bay....

C. Brewster.

A letter from George Washington to Colonel Sheldon, dated as above, informs him that one of his Dragoon Express had been captured by the British at Pines Bridge and carried into New York. Fortunately he had none of the above messages at the time. But Colonel Sheldon had work for Major Tallmadge aside from the messages, which may account for the following dated Sept. 1st and 5th not reaching Major Tallmadge until the 9th.

Setauket, September 1st, 1780.

Sir. When Culper Junior’s last dispatch came to hand he directed me to wait on him at Jericho yesterday, but my present state would not admit—therefore sent the express which handed him your enclosed—But he hath returned without any answer. The reason is he had not the counterpart. And in regard of the state of affairs in general he assured the express they remained as heretofore or as when wrote you last, nothing new, everything appeared to be at a stand, and the enemy much embarissed expecting an attack. I am sorry you have to wait so long for an answer but it must still unavoidably be lengthened until the 10th, as Culper Junior said he could not be in New York before the 8th.

Since my last the infantry have marched to Huntington and encamped there; Fanning’s Regt., to Lloyd’s Neck, Simcoe’s Rangers to Oyster Bay, and there’s in Setauket the 17th Regiment Dragoons, Some Huzzars, Some Rangers, about 20 wagons, 300 horses, 250 men, 220 mounted. They are encamped round about Capt. Nathan Woodhull’s House and Persons Lyons’. The former is the Coll. Quarters. The officers mostly lodge in Camp at night. There’s every appearance of their continuing here some time as they appear quite easy and off their guard. Am fully of an opinion that 500 good men would make prisoners of them all, if secretly conducted on your shore as well as here. If you intend to attack direct Brewster to cross the night before, and will meet him and further advise at all haphazard. Aiqlai Bqyim of Southampton is now on your shore, and positively an agent for the enemy. He hath been a long time servicable in that way, and this is his second embassy. I know it to be true and have lately had a perfect knowledge of his conduct for this three years past, and have been solicited by his friend as an assistant.

A little time past a boat from New Haven, loaded with provisions met a number of Refugees here; one of the mens names was Trowbridge, an intimate acquaintance of John Clarke; and you may depend the refugees land on your shore and hide their boats. The other day I saw a man that had the appearance of a gentleman, told me he had been three weeks concealed in Middletown and Hartford—the former being his native place; but could not find out his name. He told me he had left 20 odd Thousand Pounds of Counterfeit money of your late emissions in the hands of the Toreys—to pay their taxes with. You’ll doubtless take some notice of this information—and anxiously wait for the arrival of our deliverance, and am Sincerely your

Saml. Culper.

Major Tallmadge’s letter from Lower Salem, Sept. 13th, and General Washington’s of the 16th, throw further light upon the service. It may be noticed that practically all of Culper Junior’s stain letters were now being deciphered by Major Tallmadge, each time with an apology for so doing. He was not aware at that time that had he failed to decipher them Major André would have been able to join Arnold and the treason plot might not have been discovered until it was too late.

Lower Salem, Sept. 13th, 1780.

Sir. I have the honor to enclose dispatches from the Culpers which have this moment come to hand. As C. Junrs. was an answer in part to my last on the plan of our future correspondence, it was necessary for me to decipher it. Your Excellency will observe what he writes respecting his services and as he informs he can shorten the route on certain conditions, Your Excellency’s assurance will regulate his future services. This much I can observe respecting the man, he is a Gentleman of business, of Education and honor—Culper Senior’s frequent Expresses to N. Y. for the papers which are forwarded to your Excellency, and to resolve questions proposed by other Genl. Officers at other periods, has expended the money which has been furnished him, as we were considerably in arrears when the last money was handed him. I have just engaged a man to bring letters from N. Y. via Kingsbridge if necessary; but cannot as yet tell whether C. Junr. will deliver him dispatches—His name and services I believe are well known to your Excellency.

I received Major Humphrey’s letter of the 11th last evening, and immediately wrote to have the boat cross, which I am confident will not be delayed only by the present heavy wind and rain. Your Excellency may depend on my Exertions in the matter. I shall fold this letter very small to prevent being discovered if the Express should chance to be taken. [It was folded to size 2¾ × 4]....

Benja. Tallmadge.

It certainly was not possible at the moment to realize the importance of the messages that were now arriving. Woodhull’s inference that they contain much good intelligence is prophetic. The first is dated

Setauket, September 18th, 1780.

Sir. Your favour of the 12th inst, together with the enclosed came to hand on the 15, at 12 o’clock. I immediately set off and have done all that in me lay, and is communicated in the blank inclosed, and it contains much good intelligence, I hope all that’s needful. Our spirits are extremely low here. We Pray for your best endeavours. The times requires you to be vigilent and active. Sir George Rodney’s Fleet hath arrived. See the Paper. I have induced C. Junr. to shorten the present rout the letters take, as mentioned in the blank. It will be done in the course of ten days I hope similar to your plan proposed. I have made several discoveries of villany but have not time to write now. Forbid the boat man on with 725 to come any more, and desire Governor Trumbull immediately to grant him no favours, or else it will be too late. In my next will state the matter to you. In the greatest haste am yours sincerely

Samuel Culper.

N.B. 17th Dragoons at the Branch.

Greenfield, Tuesday morning, 6 o’clock
19th Septr. 1780.

Sir.

I have been impatiently waiting at this place for some time for the arrival of C’s Dispatches, which have this instant come to hand. A very heavy gale of wind prevented the boat from crossing at the time appointed. I hope the enclosed may be satisfactory. I shall inform Genl. Heath of what respects the French Army at New Port, agreeably to your Excellency’s orders. Enclosed is an account of expenses from C. A man is obliged always to ride to New York from the place where the boat lands and wait Culper’s answer; his expenses on the road and in the city for himself and horse must be very considerable. Your excellency will furnish such supplies, in answer to the enclosed, as may be judged necessary. I had the honor last night to receive your Excellency’s favor of the 16th inst. the contents of which shall be duly forwarded to C. Junr. I have the honor to be, with great Regard, Sir, Your Excellency’s most Obedt. Servt.

Benja. Tallmadge.

At this period the Culpers were using more care to conceal the intelligence in their letters, as will be observed upon examining Woodhull’s, dated August 27th.(126) Townsend’s were now all written with the stain. Tallmadge’s efforts to shorten the line of communication have been preserved in a series of three of his letters to Headquarters written during the month of August.

Incidentally, in his zeal he almost betrayed the identity of Culper Junior. The first letter, dated August 10, 1780, reads:

Tallmadge’s next letter in this series is dated from North Castle, August 20, 1780: and reads:

“Sir. Since my last I have made several attempts to open a communication with Culper, Junior, by the way of Oyster Bay or Cow Neck. The person whom I mentioned to Your Excellency as the properest man to engage and secure Culper’s services, was away from home, at New York, and last Monday night I sent over an Officer who formerly resided at Oyster Bay, but the person in question was then too ill to be seen. I shall still pay attention to this matter, tho the Refugee boats which frequently pass up and down the Sound makes crossing very dangerous.

“Enclosed is a letter from the person who has for a long time bro’t dispatches from the Culpers. Your Excellency will perceive he has been attacked by some of the Refugee Boats. He requests more men, as may be seen by the enclosed. Your Excellency will please to direct me in the matter. There are several Continental Crews at Stamford and Horseneck, whose duty I am unacquainted with. Perhaps one of those can be spared.

“I am sorry Lt. B.——r was drove from L.I. so suddenly as dispatches from Culper Junior were then waiting for him. I have the Honor to be Your Excellency’s most Obedt. Servt.

“Benj. Tallmadge.”

FOOTNOTES to “SECRET SERVICE SECRETS”:

[16] See Memoir of Colonel Benjamin Tallmadge, p. 130.

[17] It was this Austin Roe who fell from his horse and broke his leg while hurrying to keep an engagement with George Washington in 1790. The President was then touring Long Island and, probably without disclosing his reason to any one, requested the presence of those who had faithfully served him during the Revolution. Austin Roe had long occupied the Setauket homestead, later known as the Dering property, and still later owned by the Irwins who in 1936 moved the house to a new location. Roe’s brother, Captain Daniel Roe, was at the time occupying the Roe homestead at Port Jefferson, then called the Townsend house. Captain Nathaniel Roe was a cousin, not in the neighborhood at the time. Austin “bore the title of Captain,” his biographer says, but few knew what he commanded.

[18] Colonel Simcoe had been captured and was at the time a prisoner in New Jersey.

[19] Washington Papers, March 23d, 1780, No. 17458.

[20] Austin Roe might justly be called the Paul Revere of New York, with this difference, that instead of taking one wonderful ride Roe took a hundred. Paul Revere at his fastest speed did not equal this ride of Austin Roe that saved Newport from the British. Fifty-five miles he rode to reach Abraham Woodhull while Brewster waited to carry the message from Robert Townsend across the Sound. It gave General Washington the information that 8000 British troops were embarking at Whitestone destined for Newport, and that Admiral Graves with eleven ships was already on the way to Rhode Island to meet the French Fleet which they were assured consisted of only seven sail. The message reached Washington in time to get the information to British headquarters that an immediate attack upon New York was contemplated and therefore the forces were withdrawn from Newport before they had an opportunity to accomplish the work of destruction.

[21] On the tenth of July, 1780, a powerful fleet under Admiral Tarnay arrived in Newport Harbor, having on board some six thousand troops under the command of Count de Rochambeau. The expedition had been secretly fitted out at the instance of Lafayette, and nothing was known of it by the Americans until his return in May. On the 17th Lafayette left headquarters with full authority to arrange plans with the French commanders for future operations. Hall’s “Life of Parsons,” p. 296.

[22] As early as 1778 the British on Long Island had a method of transmitting important news that was as rapid almost as the telegraph is today. For this purpose beacons were established and a system of signals arranged. Among the papers of Major John Kissam have been preserved some of the instructions which so clearly state the eminences upon which these beacons were erected that there would be little trouble in locating them at the present day. Following are unabridged copies of these instructions:

Signals: Col. Hamilton will be so good as to place a man at the most convenient heights, to see Laurel Hill and Morris’s house. He will observe what signals are made from there—if there are 3 guns from Laurel hill and 3 fires from there or Morris’s house,

2 guns and 2 fires ditto, or

1 gun and 1 fire from ditto, and report the same to the commander in chief on board the Grand Duke at Whitestone. Ol. DeLancey, Aid de Camp.

Signals by day and night for Long Island and Kingsbridge. To be made from Norwich hill, Sutton’s hill and Flushing Heights in Queens County, L. I. viz.

1st. On the Enemy’s landing in force eastward of Norwich: by night, 1 beacon fired at each, by day 1 large smoke at each.

2d. On Enemy landing in force westward of Norwich hill; by night 2 beacons fired at each; by day, 2 large smokes at each.

Signals acknowledged from Morris’s house. By night; 1st signal, 1 rocket, 2d. signal, 2 rockets. By day none none

N.B. The fires and smoke to be kept up while the Enemy remain on the Island, or until otherwise observed. After every signal a Light Dragoon to be sent from Morris’s house to Head Quarters with the intelligence.

Mem. Norwich hill is 2 miles south of Oyster Bay, Sutton’s Hill [now Beacon hill] is 3 miles from Cowneck Point; Flushing Heights are near Ustic’s house.

Appointed by the Commander in Chief,
Wm. Tryon M. G.

Scorpion
A copy
P. Brown.

* * * * *

Hempstead Plains, July 30, 1778.

To Major Kissam. Sir, In the absence of Col. Hamilton you will take command of the Queens County Militia, & execute such measures as you shall think necessary for the benefit and protection of the County. In particular you will observe the following directions respecting the Beacons on Cow Neck and near Norwich, and take steps requisite for their being carried into execution.

Whenever any Beacons to the Eastward are seen on fire, you will immediately set fire to those under your care, making one fire or more, as you observe those to the Eastward have done, in every instance following their example: and whenever you have so done, you will send an express to the commanding officer of the King’s forces at Jamaica, informing him that 1, 2, or 3 beacons (as the fact shall be) are fired to the Eastward.

In all cases when you have certain intelligence of the Enemy being landed on this Island in force, you will fire all the 3 beacons, and dispatch an express as above with the information, always keeping up the fires until the intelligence shall have reached New York. You will of course have a distinct beacon at each place in readiness to be fired, and if it should happen in the day time, encourage the smoke as much as possible.

A corporal and 4 men are to mount guard at each place on them, night and day, always keeping a centinel looking out for signals. These men you will change weekly, or at your discretion and excuse them from all military duty. A compensation will moreover be made them in proportion to their diligence and service.

These directions are to be strictly observed by the Guard at each of the 2 places fixed on by Brigr. Genl. DeLancey for the erection of the beacons, and the guard stationed on the hill near Norwich will also observe to send an express to Cow neck whenever the beacons under their care are fired. Wm. Tryon. M: G:

* * * * *

Scorpion off New City Island, Jan. 30, 79

Signals.—If the Rebels are attacking any vessels; or landing or landed between this station and Hempstead Bay; the Signals by night are 2 fires on Lawrence Hewlett’s Point; by day, 2 smokes on the same.—If the attack is made in Cow Bay the signal by night is 1 fire on Lawrence Hewlett’s Point: if by day 1 smoke on the same.—The above signals will be answered from the Scorpion; by day by hoisting the colors, or hauling them down, if hoisted previously; by night with lights, false-fires or musquets. Philip Brown.

[23] The Spies of Washington did not record the names of the British vessels in Gardiner’s Bay but the heir to the island, John Lyon Gardiner, who was a boy ten years old when the fleet arrived, made record on February 9, 1796, in which he says: “There were eleven ships of the line and perhaps some frigates. They came in August, 1780, and went out in March, 1781. There was the ‘Royal Oak,’ 74 guns, Vice Admiral Arbuthnot, ‘London,’ 90 guns, Rear Admiral Graves, ‘Colloden,’ 74 guns, Capt Sweeny, ‘Bedford,’ 74 guns, Capt Affleck, ‘Prudent,’ 74 guns, Capt. Charles Ogle, ‘Robuste,’ ‘America,’ ‘Shrewsbury,’ ‘Europe,’ ‘Rising Sun’ and ‘Swan.’”

[24] Note. Before these accounts are finally closed, justice and propriety call upon me to signify that there are Persons within the British Lines—if they are not dead or removed, who have a claim upon the Public under the strongest assurances of compensation from me for their services in conveying me private intelligence; and which when exhibited I shall think myself in honor bound to pay. Why these claims have not made their appearance ere this, unless from either of the causes above mentioned—or from a disinclination in them to come forth till the B. force is entirely removed from the United States, I know not—But I have thought it an incumbent duty on me to bring the matter to view that it may be held in remembrance in case such claims should hereafter appear. Go: Washington. [The private account book of Culper Senior, in the Library at East Hampton, L. I., shows that he received the balance due him on August 2, 1790. There is nothing to show that Robert Townsend ever asked for or received his. Before the capture of Major André he was anxious for assurances that if he used his own money to promote the service he would be compensated at the close of the war. Later it is probable that he preferred not to risk discovery by preparing an itemized bill, as Woodhull was obliged to do.]