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Long IslandHistory

Christopher Vail: Soldier and diarist

An amazing personal story from the journal of a soldier, sailor, prisoner and patriot.

An illustration of King George III's statue being

An illustration of King George III's statue being torn down in New York City after a reading of the Declaration of Independence, July 9, 1776. Photo Credit: The American Revolution: A Picture Sourcebook

In the summer of 1775, with the news of Lexington and Concord fresh in their memories, the aroused American colonies stood on the threshold of revolution. Those who chose to fight in the new Continental Army stepped forward, one by one.

And so, a 17-year-old apprentice rope maker from Sag Harbor went to war.

“I Christopher Vail of Saggharbour, Suffolk County and State of New York enlisted as a soldier in Capt. John Hulberts company . . . July 5, 1775.”

This is one man’s Revolutionary War story, an extraordinary seven-year odyssey told in an unpublished, 18,000-word account titled “Christopher Vail’s Journal 1775-1782,’’ a copy of which is owned by the Library of Congress.

Vail is everyman. And he seems to be everywhere. His is a Long Island story and more. He joins a militia troop in Bridgehampton. He marches to Ticonderoga, N.Y. He guards cattle at Montauk. He misses the Battle of Long Island by hours. He joins in whaleboat raids on a Long Island occupied by British troops. He sails on privateers that prey on British shipping, and is captured and imprisoned in Antigua. He’s taken to London, and escapes. He goes to the Mediterranean, is captured and escapes again. He hides out in Portugal, crosses over into Spain and makes his way back to Salem, Mass. He’s in New London, Conn., when the traitor Benedict Arnold torches the city. He once more goes to sea and is captured again and put aboard the notorious prison ship Jersey, where thousands die.

Vail was 17 when he enlisted for six months in Capt. Hulbert’s company. First taking a boat to New York, the company marched north of Albany to Fort Ticonderoga, which had been taken from the British in the spring of 1775. They stayed a month. Vail’s quiet first enlistment ended as his troop escorted British prisoners south, and he headed home to Sag Harbor, arriving Jan. 15, 1776.

“I enlisted again in a few weeks as a private in Capt. John Davis’ company, and Wm. Havens 1st Lieut., in the continental service for twelve months, and was stationed at Montaug [Montauk] Point in order to guard a large quantity of cattle which was kept there belonging to several towns.

At that time there were about 1,000 cattle and about 2,500 sheep pastured on common land at Montauk Point. British warships were threatening Gardiner’s Island as well as the mainland, where they would occasionally land to try to steal cattle to feed their troops.

But in that summer of 1776, the Royal Navy was concentrated in New York Bay, where the British were making plans to attack Brooklyn. The onslaught - known as the Battle of Long Island - began and ended on Aug. 27.

Nothing extraordinary happened until 27th of August 1776 when we were informed that the British had landed on the west end of the Island. We had our orders to march up the Island to reinforce our troops, and began our march immediately, and after marching 40 miles distance we were informed that the Island was captured after a hard battle was fought, and a great loss on our side. We immediately began our retreat to Southold where we obtained vessels and carried our company over the Sound.”

Sometime that fall, Vail got his first taste of “whaleboat warfare,” which would become common throughout the war. Whaleboats, loaded with Patriot soldiers, would be rowed, and sometimes sailed, across the Sound from Connecticut to attack British-held positions on Long Island. Some were minor skirmishes, others all-out battles, and there was plenty of bloodshed.

“We at this time had information of a company of Tories that was stationed at Sautucut [Setauket] L. Island. We collected about 60 whale boats and manned them and cros’d over the Sound in a heavy blow from N. West in the night in company with the armed schooner Spy of 10 guns, Capt. Niles and arrived at the Island about 11 p.m. and divided our force so as to take their whole force by surrounding their guardhouse and head quarters at the same time. On our arrival at the guard house numbers fled to headquarters where the whole was taken. We killed 13 of the enemy and brought off 40 prisoners, and made prizes of two sloops - we had one man killed, none wounded, and the day following we returned to New Haven.”

In May 1777, Vail participated in one of the best-known raids on British encampments on Long Island. This was the brilliant attack on Sag Harbor, led by Lt. Col. Return Jonathan Meigs. With 234 men in 13 whaleboats, the raiders crossed over to Southold, carried their boats overland to Peconic Bay and then rowed to Sag Harbor. Six British were killed and 90 prisoners taken; Meigs did not lose a man.

“We landed on the west of the port about half a mile and surrounded the village at once and proceeded down to their quarters where we completely succeeded in capturing the whole force except one man. We burnt all the coasting vessels which was all loaded and laid along side the wharf and a store that was 60 feet long that stood on the wharf.”

Vail said that the British soldiers had just gotten their pay, and many had been eating and drinking heavily.

“They remained went to drinking and all got pretty well boozey. When we arrived we took ninety nine Tories. Some had nothing but his shirt on, some a pair of trouser, others trousers stocking and one shoe and in fact they were carried off in their situation to New Haven.”

A few days after the raid, Vail was discharged. But he kept coming back for more. For the next few months he joined in other whaleboat raids. A number of times they would sneak over late at night and board enemy sloops and take them back across the Sound as prizes of war. One of these raids, probably in 1778, was typical:

“The next day went with our boats across the Sound, and landed at the Canoe place on L. Island and hauled the boats up in the bushes and marched up the Island about 20 miles to a place called Speonk where we took possession of 8 or 10 whale boats, and brought them off to New London.”

Though there is no reason to question the truth of this account, it boggles the mind to imagine getting eight or 10 whaleboats from Speonk in southwestern Southampton to New London. They possibly headed south to the ocean, then east around Montauk Point.

That summer, 1778, Vail entered a new phase of his military service. He would for the next four years work as a seaman on armed ships searching for “prizes,’’ that is, British or Loyalist vessels that were themselves on plundering missions. These were privateers, private vessels sailing under a “letter of marque’’ from the American officials, allowing them to capture or destroy any enemy shipping they encountered.

In July 1778, Vail signed on with the Warren, a 32-gun frigate. On Sept. 2 they ran into a hurricane while in the Gulf Stream, and the ship was upset, lying with keel out until she righted again. Men were blown off the topsail and drowned, and the Warren was battered.

“At this time the whole horizon was likk fog. The clouds and water all mixed together. And you could not hear a man which was standing along side of you and halloring as loud as possible. The sea at this time as smooth as a mill pond and no motion to it but as the wind got steady and blowed from the N.E. the sea at once rose to a mountain. At 8 p.m. the whole n seemed on fire. It was my trick at the wheel from 8 to 10 p.m. The sea came tumbling after us looked to be half a mile high, and would brake a part of it on our gangway and go 30 feet over the bows. . . . The day following we took a brig laden with molasses from Jamaica bound to Halifax.

After the Warren sailed to Newfoundland and captured an English brig with a cargo of wine and fruit, Vail wound up in New London, where he stayed until Jan. 1, 1779. He then shipped out on the 10-gun sloop Revenge, bound for the West Indies. After capturing a schooner from Surinam bound for Halifax, Vail was put on board the prize to take her to New London.

On Feb. 13, the schooner was captured by the British and taken into St. John’s, the capital of Antigua. He and his mates were put into a two-story stone prison. It would be his home for the next 11 months and 9 days.

Our allowance per day was 1/4 lb. salt beef and 3/4 lb. bread, and water that had been to Guinea and brought back again, and millions of worms in it. Sometimes they gave us puddle water, but seldom rain water. I have frequently weighed the beef and found it seldom to weigh over two ounces. And if a bony piece you may say there was none of it. We then pounded the bone and sucked the substance, as long as we could find any substance. We generally ate it raw, for if it was boiled it would not be over an inch square. And no substance in it . . .

One day in the dividend of our beef a bony piece fell to a poor Frenchman who immediately hauled up his shoulders and said no bone, no bone, which in English is no good. An Irishman standing by and one of the prisoners says in reply to the Frenchman, by Jasus I think it is all bone ...

We tried every method that could be invented to make our escape but very few got off the Island after breaking out. If you did not leave the Island that night you was almost certain to be taken the next day, as there was 8 dollars a head allowed for every man that made his escape out of the prison . . .

Vail describes numerous attempts to escape, and although some men made it, he never did. One attempt failed when the guard they bribed took the money, then threatened to blow anyone’s brains out who attempted escape. In another, they cut a hole through the roof, but the first man out was shot as he descended the wall with a ladder.

Our rooms that we was kept in was about 18 feet square and in each room stood 2 necessary tubs for our use which never was removed until filled which was very nauseus. We generally kept up good spirits. We sold our clothes, buckles, hats & in fact every thing that would fetch a cent. As for myself I had nothing to wear but a pair of trousers worn off up to the knee and no sleeves to my shirt, which was my complete prisoner uniform.

After a while, Vail began thinking about how to make prison life more livable. He hit upon a surprising solution.

I found there was no exchange of prisoners and no chance of escape, and I being as ragged as an Indian, neither bed nor bedding to lie down upon. And an empty stomach all the time, and a ravenish appetite. I began to think what was to be done in my present situation in order to relieve my wants. I took the resolution of drawing figures on paper and staining them with my blood. I found I could make ready sale for my painting such as it was to children. And frequently in the course of the day could sell 6d worth which was a very great addition to my old allowance.

Unfortunately for Vail, another prisoner saw what he was doing, copied it and did it even better, so Vail lost all of his customers. He then found a piece of pine planking, and with his knife proceeded to carve small boats, which turned out to be a better business than blood-painting.

For one of them I had a dollar, and found my capital increasing. By this time I could have a dish of coffee in the morning bread and butter and at noon a yam with my beef & some left for supper.

After about eight months, someone took up a subscription for the relief of the prisoners at the Antigua jail. This provided for a twice-a-week additional ration of a pound of pork, a quart of rice and a quart of rum for each man.

And that added to our former allowance we lived tolerably well. They gave each man a shirt, trowses and blanket. I now began to grow rich, and had money on hand.

One day Vail was sitting at the front gate of the jail, with his legs hanging through the grating, when he saw a black woman with a servant girl. He called to the woman, who he understood was from New York and was the mistress of the captain of an English privateer. She asked what he wanted. He said he was from New York, too, and begged her to bring him some of the necessities.

She observed that she was very poor and went on to the market. About 4 in the afternoon as I still sat at the grates I saw the girl servant to the black woman coming toward the gaol with a very large waiter on her head, and soon after her misstress following came to the gaoler and demanded entrance. The door of the prison was unlocked and my black friend came into the room with a large waiter containing one quarter of a small pig, well roasted, a dish of cucumbers, 6 small loaves of bread and different kinds of vegetables with of good punch. And about 20 cents in cash. All which I very thankfully received and selected my particular friend and sat down with a thankful heart. Nor never shall I forget the donor. She also gave me about 20 cents per week during my stay at this place.

Vail then opened a new line of business. He would buy a new blanket from an Antiguan for 20 cents, pay a tailor another 20 cents to make a jacket out of it, then sell the jacket for a dollar.

On Jan. 11, 1780, all of the prisoners were taken out of the jail to make room for some newly captured French seamen. Vail and the other prisoners were distributed aboard the warships in the British fleet, which were by then doing regular battle with the French Navy. The French had joined in the war on the American side in 1778. Vail was put aboard the 74-gun Suffolk. The problem for the prisoners was that the British expected them to participate in the fighting.

We had frequently been called to quarters and threatened several times to be punished if we did not take an active part but we always refused the orders and risqued the consequences. ...

When the Spanish joined the French on the American side, pressure on the prisoners to take part in the British ship’s battles became more intense. The captain even threatened them with flogging.

We told him that we were American prisoners of war and would not go to quarters. He ordered us to the quarter deck and asked us if we meant to raise a mutiny. On our return from the quarter deck I heard the boatswan observe them I like them better for their conduct. The next day came, the drum beat to quarters, but not one American started an inch.

On July 8, 1780, the entire gang of prisoners was ordered onto another warship bound for England as part of the protection for 40 merchant ships. On board were a number of disabled men, and when the prisoners again refused to do sea duty, junior officers took canes and crutches from the disabled and beat many of the prisoners unmercifully. Vail was later transferred to a British merchant ship, where the treatment was better. But living still was hell.

The whole stock of provisions on board except the flour had been condemned six months before as unfit for use but we had no other. It consisted of white bread, black beef, yellow pork, and bunches of sour oat meal and blue butter. The bread you could take it in your hand and crumble it all to atoms, and was full of weavels and worms. The beef all but rotten and black, the pork nothing but yellow rust and the oat meal not fit for hogs. The butter had not even a streak of light color in a firkin [a quarter-barrel]. Twice a week we had a plumb pudding and every day a good drink of grog. We frequently toasted the biscuit and put on the black butter and made it into toast. Other times made the oatmeal into mush, and put in the pickle of the beef and seasoned it. We lived in this manner until we arrived in England.

At this point Vail’s status as a prisoner becomes confusing. He was allowed to go ashore at Falmouth, England, where he escaped. He signed onto the 20-gun privateer Amazon. He knew the Amazon would be looking for ships sailing under the flag of the French, who were American allies. But that, he reasoned, was better than being “impressed’’ (taken by force) to serve on a regular British warship. On Nov. 30, the Amazon sailed into port at Lisbon where Vail saw a chance for freedom.

I got liberty one day to go on shore at Lisbon. As soon as I landed I inquired for the French consul and went to his house. Found him a very agreeable old gentleman. He provided me a dinner and a bottle of wine.

The French consul also arranged for Vail to obtain both Portuguese and Spanish “passports.’’ (Vail probably meant visas.) He gave Vail some money and sent him on his way by land, river and ferry to Cadiz, Spain, passing over the Portugal-Spain border at the Guadiana River.

The buildings in this country is very mean, the inhabitants poor and the living wretched. . . . The general living is cabbage and fish boiled together and plenty of olive oil added to it. We had plenty of bread and wine and cheap. My whole expense from Lisbon to Cadiz 300 miles did not cost me above $6.00. The houses of entertainment has no floors nor furniture. The traveller and hill put up together under the same roof.

After crossing over the river into Spain, Vail took a boat down to its mouth, at Ayamonte, where the Guadiana spills into the Gulf of Cadiz. In this large town he got into a religious misunderstanding.

I was one morning in the market at this place when the host came along. The whole number of people in the market fell on their knees and went to prayers except myself. The Fryar . . . appeared very angry as I did not kneel, and I was unaquainted with freedom and religion. And on my return to the tavern where I put up I mentioned the circumstance to the landlord. He observed to me when I was in Rome I must do as the Romans do. I afterwards found . . .

On arrival in Cadiz, Vail found an American agent, who told him to find a boarding house unity to leave presented itself. In February, the agent gave Vail $4 and put him aboard a French warship bound for Bordeaux. They never got there. They came onto a British warship, and after a vicious battle - with Vail manning a 12-pound cannon - limped back into Cadiz. He then found a ship bound for Salem, Mass., and he returned to New London May 5, 1781. He had been away for a little more than two years and four months.

In two days, Vail went back to sea. During the summer he was aboard the privateer Jay, which captured nine vessels, including two English privateers, and took them back to New London. After being refitted, the Jay was about to leave New London on Sept. 6 when Vail found himself involved in yet another historic revolutionary event - the burning of New London by the notorious traitor Benedict Arnold.

As a move to divert Continental troops away from their march on Yorktown, Va., Arnold proposed an attack on New London, an area he knew well since he was born and grew up in nearby Norwich, Conn. (the same small town in which Vail would spend most of his adult life and where he would later die). But Arnold did more than attack. He had his men put the torch to the city, and to nearby Fort Griswold, commanded by Lt. Col. William Ledyard.

The town was full of merchandize and time after the British arrived nearly the whole town was in flames. . . .

The British finally succeeded and entered the fort. Col. Ledyard immediately delivered up his sword which they received and run him through the body and killed him with it. And a general massacre here took place. Every man run into the barracks to save himself but was pursued and murdered. I know of one man who told me they put the muzzle of the musket to his mouth and fired down his throat. The ball came out about 3 inches below the jaw. A cousin of mine in the fort had his skull cut open in 3 places, his back cut to the bone in 3 or 4 places and 10 bayonet wounds in his body. After the massacre was over 74 of our citizens, heads of families, within 4 miles laid dead. The wounded was all put into a wagon which stood at the fort on the top of the hill and then the wagon was set a rolling down the hill I suppose 50 or 60 rods where it brought up against a rock. The people told me the shock hurt them more than their wounds.

Three days later, Vail volunteered to go aboard the warship Dean, where he ran into more bad luck. Vail’s ship was captured by two British frigates and he was taken to Wallabout Bay in New York Harbor. He was put aboard the dreaded prison ship Jersey, one of a number of British prison ships in which an estimated 11,500 Patriot soldiers would die. Vail describes the rotting food, crowded conditions with bodies piled upon bodies, lack of air, and death all around.

Here we suffered very much for food and fresh air. We were in No. 1150 on board and all put down between decks. At sun down there was as many people lay on deck as to touch each other all round the deck and as many hammocks as could sling over head. And the fore part of the ship full of sick prisoners with the fever. There was only one passage to go on deck at a time. And if a man should attempt to raise his head above the grate he would have a bayonet stuck in it. Many of the prisoners was troubled with the disentary and would come to the steps, and could not be permitted to go on deck, and was obliged to ease themselves on the spot. And the next morning for 12 feet around the hatches was nothing but excrement ...

There was all kinds of business carried on. Some playing cards, others swearing, stealing, fighting, some dying &c. When a man died he was carried up on the forecastle and laid there until the next morning at 8 o’clock when they were all lowered down the ship sides by rope round them in the same manner as tho’ they were beasts. There was 8 died of a day while I was there. They were carried on shore in heaps and hove out the boat and on the wharf, then taken across a hand barrow, carried to the edge of the bank, where a hole was dug 1 or 2 feet deep and all hove in together.

Vail was on the Jersey when he heard the news of the surrender of Charles Lord Cornwallis at Yorktown, on Oct. 19, 1781. This pretty much ended the war, although it would not become official for another two years.

We heard the firing of cannon from the Jersey for rejoicing and whenever our people fired the British would fire from their batteries so as to confuse that people should not be informed of Cornwallis capture.

Vail was soon released in a prisoner exchange. On his way up the Norwich River heading for Norwich, Conn., where he was planning to live, he came down with a fever.

I staggered and realed like a drunken man. I got to the house that evening. I soaked my feet in warm water and I soon lost my senses for 27 days ... In about six weeks I was able to walk about and was asked whether I should go to sea any more. I told the person who asked me that I never would if I begged my bread from door to door.

But Vail’s resolve weakened as soon as salt air refreshed his nostrils. In the middle of March, 1782, he was in New London, and he went to sea again. In a flurry of privateering activity off Montauk Point and Block Island Sound, his ships captured a number of prizes that were sailed back to New London. Vail ended his role in the Revolutionary War in the summer of 1782. He was 24 and would live to be 88.

This is how Christopher Vail ends his journal:

This was in August. After this I remained on shore until November when I got married and remained at home until the next spring, when peace took place.

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