Whale Boats on the Hudson

The War Years (1775-1783)

October 12, 2017
by Phillip R. Giffin Also by this Author


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By March of 1778 Maj. Gen. Israel Putnam, “Old Put” to his men, was exhausted.[1] He had been writing to General Washington for months begging for retirement. His wife had died recently in his encampment and the general was worn out from his impossible assignments. His two under-strength brigades had been working in the ice, snow, and bitter wind since January constructing a massive complex of fortifications on the banks of the Hudson River at West Point, New York. The bastion was beginning to take shape, but it was months away from completion and with the spring thaw Putnam would have too few men, materials, and cannons to prevent the British Royal Navy from pushing up the river and blasting past his unfinished ramparts.

The men of Colonel Samuel Webb’s 9th Connecticut Regiment had been working on the wind-swept, frozen banks of the Hudson River since late January.   Among them was my distant grandfather, Sgt. Simon Giffin of Capt. Caleb Bull’s Company; he was keeping notes of their arrival in his journal.

January 27, 1778 at Fishkill, NY a cold but clear morning. We marched down to the place [Constitution Island] that Ft. Constitution was built on. There we made a halt and marched over the North River… and marched back again for there was no place to lodge there on the west side of the river so we … went into the woods and made fir beds to rest on the snow.   We made a hut that 15 of us lay in pretty warm considering the weather being so cold.

The 9th Connecticut spent the next two months hacking a road out of the hillsides and hauling cartloads of pickaxes, shovels, logs, and lumber up to a small plateau where they were building barracks for themselves and breastworks for heavy cannons. Fort Webb was one of six separate fortifications and barracks built into the hillside at the bend of the Hudson at West Point.   The fort was located some 300 feet above the west bank of the river.[2] Two similar gun batteries were constructed on the ridgeline to the south at roughly the same elevation (Fort Wyllys and Fort Meigs). All three consisted of thick breastworks of logs, stone, and mud topped with cannons overlooking the southern approaches up the Hudson River. Above them loomed Fort Putnam at about 400 feet above the River, and Redoubt No. 1 on the top of the plateau at about 800 feet elevation. Below them on the flat plain at the bend in the river was the largest of the fortifications, Fort Arnold (later renamed Fort Clinton after Gen. Benedict Arnold deserted to the enemy).

A heavy iron-chain resting on a log boom was stretched across the river from Fort Arnold to Constitution Island as a barrier to enemy ships sailing upriver. On the island there were seven more redoubts (earthen fortifications). Enemy warships navigating upstream around the bend in the river would have to slow and maneuver while gun batteries on both sides of the river rained cannon balls down on them. Then, just as they rounded the bend in the river, they would be confronted with a massive iron chain resting on log booms.

The first cannons arrived at West Point in March. Sergeant Giffin wrote in his journal …

March 25, 1778 … This day there were 2 field pieces and one howitzer brought to West Point. And the first gun that ever was fired on West Point this evening.

What he doesn’t say is that there were no dray horses available at the post. If the guns were positioned in the batteries above the river, there were teams of men assigned the task of hauling those three heavy cannons through the mud, up the hillsides, and into position.   Possibly Giffin described the scene in a letter home to his wife Lydia, but he seldom provided such details in his diary.

Four days later Sergeant Giffin was ordered to join a reconnaissance patrol to be sent down the Hudson River to explore enemy activities on the river. He noted in his journal,

March 29, 1778 Sabbath orders came to have two whale boats manned with 1 commissioned officer, 2 sergeants, 2 Corporals, and 70 privates to go on a scout down the North River. I was ordered to go as one of the sergeants, (and) to parade at 12 o’clock in the forenoon. (Later) when I did parade, I was ordered to tarry until the next morning for Major Humphreys. Nothing [else] remarkable [happened].

The commander of the raiding party, Lt. Col. David Humphreys, was a fast rising young Continental Army officer, twenty-five years old, recently appointed brigade major to Gen. Samuel Parsons. [3] In December 1778 he would go on to become aide de camp to General Putnam, in May 1780 aide de camp to Gen. Nathanael Greene, and in June 1780 aide de camp to General Washington. No American Army officer has ever served as an aide to more distinguished leaders. As a testament to his valued service, Humphreys stood beside General Washington during the ceremonies following the final major battle of the war at Yorktown; and he was given the honor of receiving the British battle flags as they were presented to the Continental Army. After the war Humphreys would be known as the Poet Laureate of the American Revolution. [4]   In his poem, “The Happiness of America” he reflected on some of the general officers, with whom he “learnt the martial art.”[5]

Shall I tell from whom I learnt the martial art,
With what high chiefs I played my early part?
With Parsons first, whose eye with piercing ken,
Reads through their hearts the characters of men.

… Then how I aided in the following scene
Death daring Putnam, then immortal Greene.
Then how Great Washington my youth approved
In rank preferred and as a parent loved.

Unfortunately he did not write about his hair-raising adventures on the Hudson in March of 1778, or of the enlisted men who served with him. For that we have Sgt. Simon Giffin’s terse description of the events.

March 29, 1778 Sabbath:   Orders came to have two whale boats manned with 1 commissioned officer, 2 sergeants, 2 Corporals, and 70 privates to go on a scout down the North River. I was ordered to go as one of the sergeants, (and) to parade at 12 o’clock in the forenoon.

[Later] when I did parade, I was ordered to tarry until the next morning for Major Humphreys. Nothing remarkable.

March 30 Monday: This morning I went a … to see if I was to go down the river with my boat and my orders were to be ready at a moment’s warning. It rained and snowed most of the day. Nothing remarkable.

Humphrey’s scouts waited two days while a storm of wind, rain, and snow swirled down the Hudson from the North. Finally, on the morning of March 31 the men were issued two days’ allowance of rum (½ pint) and then marched down to the wharf at West Point.   Waiting there were several whaleboats, sturdy skiffs of twenty-five to thirty feet in length propelled by a single sail and eight to ten oarsmen, plus a man on the rudder. The boats had upward-pointed bows at both ends, enabling the crew to launch, maneuver, or beach their craft quickly in any direction.

From West Point the scouts launched their small fleet into the current, set their single sails, and coasted downstream some fifteen miles to the King’s Ferry Crossing, pulling their boats up onto the west bank of the river at Verplanck, New York.   That afternoon they were joined by more boats and men; but they also lost one of their companions. An unnamed private from the patrol deserted and Major Humphries delayed their departure to explore the man’s motives. Was the man heading home to his wife; or was he taking the plans for their raid to the enemy? Exercising some caution, Major Humphreys ordered the men to find lodgings for the night. Giffin reported the day’s events in his journal.

March 31 Tuesday: This morning Major Humphrey sent for me to get ready with my men to go down the North River and he gave me an order to draw 2 days allowance of rum. We set out from West Point at 9 o’clock in the morning…. [By 2 we] rowed as far as Kings’ Ferry and joined the [others?] at about 2 o’clock in the afternoon. We had one man desert from the party which detained us the rest of the day. Orders came to lay out our lodgings and cook provisions. Lodged at a very poor man’s. He had nothing in the house to eat but bread and salt and he had 4 children almost naked. We helped him cook some flour by the fire.

April 1, 1778 Wednesday: This day we rowed down the river as far as Tarrytown. Landed there with 8 boats. Lodged there. Rained hard all night.

At dawn on April 1, the river was running high and fast with snow melt and rain as the raiders launched their flotilla of eight boats into the swollen river.   The current grabbed the boats and sent them careening downstream. At Tarrytown, New York, some twenty-eight miles from Verplanck, they pulled ashore and went in search of lodging for the night. Giffin noted, “It rained hard all night.”

On Thursday morning, April 2, Giffin drew rations and rum for the men and they again pushed out onto the Hudson. They had not gone far when the storm from the north intensified, bringing high winds, lightening, and thunder. The sail on their boat was shredded by the winds, and the men struggled to control their craft. Our dour sergeant noted that it was “exceedingly hard for the lads.”   Soaked to the bone with rain and exhausted from the struggle to keep their boats pointed downstream, the raiders swept past an enemy fort (possibly Fort Washington or Fort Lee) and a British warship.

Giffin noted, “Thinking to obtain our end [demise],” the men waited for the roar of enemy cannons, but no shots were fired as “the guns were wet and unfit to perform.” In storms the wind would scatter the priming powder; the touchholes of cannons and flash pans of muskets were covered so the rains would not soak them, making it impossible for either side to load and fire. Storms undoubtedly saved countless lives during the Revolution as weapons misfired and battles were delayed for better weather (see for instance Giffin’s notes for the Battle of Brunswick, New Jersey on June 22, 1777). Giffin described the scene in his journal:

April 2, 1778 Thursday: Drew provisions and rum. Orders came to embark on board our boats but we had not got far before our sail was torn apart. The wind blew hard down the river and the thunder and lightning. [It was] exceedingly hard for the lads …

We rowed down below the Fort [Washington ?] and by one Man of War thinking to obtain our end, but our guns got wet and was unfit to perform our purpose so we was ordered to row back again. got as far back as to be in sight of Tarrytown on the west side of the river. Lay cold and wet in our boat and but little to fear.

Having swept down the rain swollen river past an imposing array of British cannons, the raiders faced about and hauled their boats back upstream in the teeth of the gale passing the same menacing but silent batteries of enemy cannons.   As usual, Giffin refused to embellish the dangers or miseries of his adventure. After hauling their boats back upstream the raiders tied up on the west bank of the river within sight of Tarrytown where they spent a cold night in their open whaleboats exposed to the wind and rain.

The next morning (April 3, 1778), cold, wet, stiff and exhausted, they set off again upriver. At midday they put ashore at Haverstraw Bay below Stony Point where they “ate dinner.” What were they eating, cold boiled beef and hard tack biscuits? Did they risk making camp fires to warm up and dry their clothing? Giffin doesn’t say. That afternoon they again launched their boats into the river and rowed upstream the last few miles to the King’s Ferry landing where they “lodged” for the night.

On the morning of the 4th Giffin’s raiding party lay by the King’s Ferry landing, waiting to see if enemy warships would come upriver after them. Giffin reported that the enemy ships at Tarrytown fired several cannons at the Americans but he did not know if anyone had been hit. By afternoon, satisfied that a counterattack was not imminent, the raiders crossed to the east bank of the river, left their whale boats at Verplanck, and hiked back up the river to West Point.

April 3, 1778 Friday: This morning rowed up the river as far as Haverstraw Bay [below Stony Point]. landed and ate our dinner. Set out from there and got to King’s Ferry. Lodged there.

April 4 Saturday: This morning lay by watching the ships and the 2 tenders motions to see if they are going to come up the river, but they lay still at an anchor abreast of Tarrytown and fired several cannon at our people but to what the effect was I cannot say. We left the boats … and came up the River to West Point.

            As an interesting postscript to the above incident, in December 1780 Colonel Webb’s Regiment was no longer stationed on the Hudson River but the leader of the previous expedition, David Humphreys, was still there. By then he had been promoted to lieutenant colonel and was serving as an aide de camp to General Washington.   Washington asked Humphries if he would undertake another audacious whaleboat raid downriver. [6] American spies in New York City had reported that the two senior enemy generals in the city, British Gen. Henry Clinton and Hessian Gen. Wilhelm von Knyphausen, were living in homes close to the banks of the Hudson River. Raiders in whale boats arriving in the black of night just might be able to capture the enemy’s two senior generals and carry them off to New Jersey.

Humphreys volunteered and set off down river with a small party of raiders; this time he took thirty men and four officers in two whale boats and a barge. Once again the weather did not cooperate. A blustery north wind sent Humphreys’ raiders swirling downriver out of control past British ships and batteries along the full length of Manhattan Island and beyond. One of the whale boats was beached on Staten Island and the other crossed Raritan Bay and landed on the New Jersey shore. The large, unwieldy barge ran aground before it reached the north end of Manhattan, landing on the New Jersey shore somewhere near Fort Lee. The crew attempted to dray (tow) their flat-bottomed scow back up the Hudson River with ropes but the wind and current were too strong.   The raiders were forced to abandon their barge and set off for the long march up the east bank of the Hudson to New Windsor, New York, a wintery trek of some ninety miles.

Unfortunately for future generations, the poet laureate of the Continental Army failed to take advantage of his opportunity to immortalize the “whale boat raiders of the Hudson River,” and Grandfather Giffin lost another chance for fame. The history books tell us that David Humphreys was famous in his day both for his poetry and for his rich sense of humor. He was no Samuel Johnson or Robert Burns, but his poetry was widely appreciated.   Today his serious work seems somewhat serious, heavy, and elegiac but in his day he was also well known for his humorous doggerel.   In one of his most famous pieces of doggerel, “The Monkey who shaved himself and his friends” he tells a cautionary tale for all barbers and writers.[7]

His poem is the story of a town barber who trained his pet monkey, named Jacko, to shave customers for their entertainment. Jacko practiced on the barber’s pet dog and cat with many a nick and slice; and then decided to work on himself.

… He lathered his beard and whiskers…
and then with the razor in his dexter paw,
around he flourishes and slashes
‘til his face is seamed with gashes….

He cocked to shave beneath his chin;
Drew razor swift as he could pull it.
And cut from ear to ear, his gullet.

Who cannot write, yet handle pens,
Are apt to hurt themselves and friends.
Though others use them well, yet fools
Should never meddle with edge tools.

In all likelihood, as they took a wild ride down the Hudson River in April 1778 neither Colonel Humphreys nor Sergeant Giffin knew that the other man had a sense of humor; and in that they were at least half right. From reading his entire diary, it seems unlikely that anyone ever accused my distant grandfather and hero, Sgt. Simon Giffin, of having a sense of humor.


Special thanks to distant cousin Robert E. Moser who provided a photographic copy of our mutual Grandfather’s Diary for research and publication purposes. This was the best retirement gift I could ever hope to receive. For more about Simon Giffin, see The Diary of Quartermaster Sergeant Simon Giffin of Col. Samuel B. Webb’s Regiment 1777-1779 and The Regimental Record Book of Quartermaster Sergeant Simon Giffin 1779-1783, microfilm and bound copies in the Connecticut State Library and Archives (CSLA).

[1] William Cutter, The Life of Israel Putnam Major General in the Army of the American Revolution (New York: Coolidge: 1850), 316, available at archive.org.

[2] Colonel Eugene J Palka. & Lt. Col. Francis A. Galgano, The Military Geography of Fortress West Point:A Geographical perspective of the role of West Point in the Defense of the Hudson River Valley during the American War of Independence (US Military Academy West Point: 2001), http://www.westpoint.edu/gene/siteassets/sitepages/publications/the%20military%20geography%20of%20fortress%20west%20point%202001.pdf, accessed July 27, 2015.

[3] Charles S. Hall, Life and Letters of Samuel Holden Parsons 1737-1789 (Binghamton, NY: Otseningo, 1905), 162-63, available at archive.org. See also Francis B. Heitman, Historical Register of Officers of the Continental Army during the War of the Revolution (Washington, DC: Lowdermilk, 1893), 308, available at archive.org.

[4] Frank Landon Humphreys, Life and times of David Humphreys: Soldier, statesman, poet, Vol II (New York: Putnam, 1917), 320, 325, 332, available at archive.org.

[5] Samuel Kettell, Specimens of American poetry and critical biographical notice, Vol. 1 (Boston: Goodrich, 1829), 271-72, available at archive.org.

[6] Page Smith, A new age now begins: A people’s history of the American Revolution, Vol. ii (New York: Penguin, 1976), 1339-40. See also Humphreys, Life of David Humphreys, Vol. I, 194-97.

[7] Kettell, American poetry Vol. II, 319-321.


  • Michael: Thanks for your note. Isn’t it great that all the older copies of the Journal are available online. I read your fine piece about King’s Ferry. Great Grandpa, Co. Sergeant Simon Giffin was stationed and/or passed through the area repeatedly. His regiment was staying in “Barracks No. 2 above Peekskill” in early October 1777 when the British took Forts Montgomery & Clinton. They then moved up to defend Kingston, but arrived too late to help. Then back to Peekskill where he “lodged at Col. Drake’s (a local Inn I presume). Thanks again, Phil

  • From one Phil to another, a very nice article. Learned something new. Very familiar with all those places: Fort “Monty,” Constitution Island, West Point, Stony Point, Kings Ferry, Verplanck, etc. Ruins of Fort Webb are not much, just some stones in the ground, but they are there. Ruins of Fort Wyllys which is just the stone foundation is far more impressive. In fact, I think Wyllys is the best of the remaining original West Point forts. Fort Putnam is neat, but rebuilt anew on the same location (forget when). I presume security at West Point is rather tight anymore, so I doubt anyone can wander around exploring like we did years ago….

  • Phil W.: Thanks for the kind words. I worked in New York and Jersey years ago and barely noticed the Hudson (the business world does that to a person). Glad to know there are some stones to see at Fort Webb, and more at Fort Wyllys. When I write about the palisades I’m thinking “palisades of the Columbia in Oregon.” I must travel the Hudson someday soon, and maybe watch a Nor’easter come roaring down the gorge. Regards, Phil G

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