Henry Beekman Livingston 
In the summer of 1776 Lt. Col. Henry Beekman Livingston was sent with three companies of the 2ndNew York Regiment to guard the Eastern end of Long Island. In July Henry wrote to George Washington to explain the disposition of his troops. He had assigned one company to Montauk Point, one to Shelter Island and one to Oyster Pond Point (present day Orient Point.) He was guarding more than 1,600 cattle, 500 horses and 10,000 sheep. The local committee of safety had given him two canons but no ammunition for them. He hoped Washington could send him some because he felt “they would be of Service to us in the Enemy Should ever take it in their Heads to visit us.”[i]
            On July 20th Nathaniel Woodhull, a member of the New York Convention and a general of the Long Island militia wrote to Washington. At the end of his letter he asked that Henry and his men be left at their current post and not removed. He feared “the Inhabitants would totally abandon the Country should those troops be drawn off.”[ii]This was a fear that Henry shared and the loyalty of the citizens of Long Island would play a major role in the events of the next couple of months. The British fleet had arrived in New York Harbor in early July. Everyone was holding their breath to see where the British would attack.

32,000 troops in New York Harbor

\”I\’ve got the weirdest feeling we forgot something\”
            On August 22, 1776, the British began landing on Long Island near present day Brooklyn, on the other end of Long Island from Henry’s position. By the end of the month the British had pushed Washington and the main army off Long Island, leaving Henry and his men trapped behind enemy lines.
            All the while Henry was receiving intelligence about what was happening on the west end of the island he held his post. On August 30, he watched, what he took to be, three British frigates, a brig and a sloop sail into Long Island Sound. He realized that “Communication by water between this and New York is now cut off.” Henry offered to attack the British rear if he could have reinforcements from Connecticut. The country was exposed to the “Ravages” of the enemy and he was seeking orders.[iii]
            Henry wrote to Washington again the very next day. The situation was getting worst. The British ships were still in the sound, General Woodhull had been wounded and captured by the British (he would later die of his wounds) and British horsemen were disarming the population. Henry began to march his men west hoping to raise the local militias as he went and perhaps attack the British.[iv]

Right before Woodhull accidentally fell on that soldiers
sword over and over again

            On September 4th, Washington finally had a calm moment to write back to Henry. He was not encouraging. He wrote: “it is not in my power to give you any instructions for your Conduct…” He encouraged Henry to deny the British forage but ultimately left Henry’s fate up to Henry.[v]
            Henry had not idle while waiting to hear from Washington. As he marched west, he had gathered about 150 militia men.  Unfortunately, they all deserted when they heard that Washington had abandoned Long Island. At about the same time he received a letter from the people of the town of Huntington, begging him to “for Gods Sake” not advance toward their town as they had already surrendered to the British and feared that the presence of his men would cause the British to destroy the town.
            Henry saw that his options were getting slimmer and slimmer. He began to retreat. Along the way, he disarmed any loyalists he found. By the time, he was ready to cross the Long Island sound to Connecticut he had gathered 236 small arms, 6 canons, 5 casks of gunpowder, 2 and ½ boxes of musket balls, 190 cartridge boxes, 160 full powder horns and 153 bayonets.[vi]

A replica of the type of boats Henry and his men used to
cross Long Island Sound. Not shown: sea sick sheep.

Henry and his men loaded into whale boats, somehow avoided the British navy and made it to Connecticut on September 2. He immediately began planning a return to Long Island. Shortly after writing his letter to Washington on September 11, Livingston and his men rowed back to Long Island. They landed at Shinnecock and carried off 3,129 sheep and 400 cattle. One of his companies also headed into Setauket, to break up a tory militia that was forming there. They attempted to arrest the captain of the Tories, Richard Miller Jr., but he resisted and was shot. He soon died of his wounds. 

Don\’t let the doe eyes fool you, Oliver Delancey Jr
would put a price on you.
            This raid proved to be too much for another loyalist, Oliver Delancey. The Delanceys had been long time political foes of the Livingston family. Because of this raid, Oliver Delancey put a bounty of 500 pounds on Harry’s head. Harry offered to put the same price on Delancey’s head if Washington agreed.[vii]
            Henry’s time on Long Island was reaching its end though. During October of 1776 Henry worked on a plan for a large raid on Long Island involving his troops as well as troops from Connecticut and Massachusetts. He had Washington’s full support but when the whale boats he had been promised failed to show up it appears the plan was aborted. In November of that year Henry was promoted to colonel and given command of the 4th New York Regiment in the Hudson Highlands. His duties carried him away before he had a chance to further harass the British on Long Island.

[i] “To George Washington from Lieutenant Colonel Henry Beekman Livingston, July 1776” Founders Online, National Archives
[ii] “To George Washington from Nathaniel Woodhull, 20 July 1776” Founders Online, National Archives.
[iii] “To George Washington from Lieutenant Colonel Henry Beekman Livingston, 30 August 1776” Founders Online, National Archives
[iv] “To George Washington from Lieutenant Colonel Henry Beekman Livingston, 31, August 1776” Founders Online, National Archives.
[v] “From George Washington to Lieutenant Colonel Henry Beekman Livingston, 4 September 1776” Founders Online, National Archives. I couldn’t find any reference to Washington agreeing to a price on Delancey’s head.
[vi] To George Washington from Lieutenant Colonel Henry Beekman Livingston, 11 September 1776” Founders Online, National Archives.
[vii] “To George Washington from Lieutenant Colonel Henry Beekman Livingston, 24 September 1776” Founders Online National Archives