The regular soldiers and officers marching towards the Lexington militia were in an understandably foul mood. The expedition, under the command of Lieutenant-Colonel Smith of the army and Major John Pitcairn of the Royal Marines, consisted of over seven hundred men. The force was composed of one company of marines, and the grenadier and light infantry companies of eleven different regiments.
Also present with the column were the Loyalist guides who either volunteered or were recruited to assist the mission to Concord. Little has been written about the role Loyalists played in Gage’s military operation. A review of primary sources, including Loyalist claims for compensation after the American Revolution, suggest that at least six loyalists were recruited to assist Lieutenant Colonel Smith’s expedition by navigating colonial roads and assisting troops in locating military stores in Concord.
Among the guides were former Harvard classmates and friends Daniel Bliss of Concord and Daniel Leonard of Taunton. Both were well established attorneys who were forced to flee to the safety of Boston in 1774. It was suspected by many Massachusetts Loyalists that Leonard was the anonymous author “Massachusettensis”, who had published a series of pro-government letters drafted in response to the political arguments of John Adams.
Dr. Thomas Boulton of Salem and Edward Winslow Jr. of Plymouth also voluteered for the mission. Boulton was a vocal supporter of Crown policies towards Massachusetts and was forced to flee to Boston in 1774. Winslow held several political and legal posts in Plymouth County. Sensing a radical shift in the political mood in October of 1774, he abandoned his estate and also retreated to Boston.
Another Loyalist was William Warden. Warden was born in Boston and was a shopkeeper, grocer and barber. Unlike many of his station, Warden had been opposed to the political and violent activities of the Massachusetts “patriots” since the Stamp Act.
It appears the guides were interspersed throughout the column. Lieutenant William Sutherland of the 38th Regiment of Foot references on two separate occasions a “guide” attached to the front of the column. “When I heard Lieut. Adair of the Marines who was a little before me in front call out, here are two fellows galloping express to Alarm the Country, on which I immediately ran up to them, seized one of them and our guide the other, dismounted them and by Major Pitcairn's direction gave them in charge to the men.” In a separate letter, Sutherland describes how a Loyalist guide identified a captured American prisoner as being a person of importance. “I mett coming out of a cross road another fellow galloping, however, hearing him some time before I placed myself so that I got hold of the bridle of his horse and dismounted him, our guide seemed to think that he was a very material fellow and said something as if he had been a Member of the Provincial Congress.”
The troops and guides started crossing the Charles River by boat at ten o’clock at night. According to the Reverend William Gordon, “On the first of the night, when it was very dark, the detachment, consisting of all the grenadiers and light infantry, the flower of the army to the amount of 800 or better, officers included, the companies having been fitted up, and several of the inimical torified natives, repaired to the boats, and got into them just as the moon rose, crossed the water, landed on Cambridge side, took through a private way to avoid discovery, and therefore had to go through some places up to their thighs in water.” For the next two hours, the entire expedition stood in the freezing marshes of Phips Farm until rations that they did not need arrived and were handed out.
When the expedition finally got under way at two o’clock in the morning, Colonel Smith soon realized that the entire countryside seemed to know of its existence. As he reported days later, “notwithstanding we marched with the utmost expedition and secrecy, we found the country had intelligence or strong suspicion of our coming, and fired many signal guns, and rung alarm bells repeatedly.” Realizing that the expedition was running behind schedule and that the success of the mission was in jeopardy, Smith halted the column upon reaching Menotomy. There, he gave his men a short rest and summonsed Pitcairn. He ordered the Major to take the six companies of light infantry and “march with all expedition to seize the two bridges on different roads beyond Concord.” Pitcairn set off immediately, pushing his detachment hard, and sent forward an advance guard consisting of Lieutenant Jesse Adair of the Royal Marines, loyalist guide Daniel Murray, several other officers and eight light infantrymen.
As Pitcairn’s force mobilized, the advance guard captured two men on horseback: Asahel Porter and Josiah Richardson of Woburn. As the two riders were taken into custody, signal guns and alarm bells began to sound. Hearing the alarms, Smith ordered an officer to return to Boston to request reinforcements.
At the front of Pitcairn’s column the sound of many galloping horses was heard, and into the ranks of the advance guard rode Major Mitchell’s party which had earlier captured Revere and three Lexington riders. As Lieutenant William Sutherland of the 38th Regiment of Foot remembered, “[we] were joined by Major Mitchell . . . and several other gentlemen who told us the whole Country was alarmed and had Galloped for their lives, or words to that purpose.”
Yet, Pitcairn was determined to still press ahead to Concord. As the expedition advanced, a third alarm rider, Simon Winship of Lexington, was captured. However, unlike his two predecessors, he refused to dismount and had to be dragged off his horse at gunpoint.
The column encountered other individuals on the road that morning both on horse and on foot. Each of them, when questioned by the officers, emphasized that a large body of militia was gathered in Lexington and would resist the regulars if they continued their march to Concord.
As the column crossed into Lexington, Lieutenant Sutherland physically collided with Benjamin Wellington, a thirty-one-year-old Lexington resident who had his musket and bayonet in hand. “I . . . mett one of them in the teeth whom I obliged to give up his firelock and bayonet, which I believe he would not have done so easily but for Mr. Adair’s coming up.” Wellington was forced to surrender his musket and was then ordered to go home. Instead, he ignored the instruction and hurried back to the village common. He rearmed himself with another musket from the town’s stock.
As the column closed in on Lexington’s common, a British sergeant reported that a party of colonial horsemen rode out from the village and shouted, “[you] had better turn back, for you shall not enter the town!” One of the mounted men then “presented a musquet and attempted to shoot them, but the piece flashed in the pan.” According to Lieutenant Sutherland, another individual fired at him from the vicinity of Buckman’s Tavern. He reported this to Pitcairn who then galloped to the front of the column, halted the men and ordered them to load their muskets and fix bayonets.. “On this, I gave directions to the troops to move forward, but on no account to Fire, or even attempt it without Orders.”
William Sutherland noted “shots fired to the right and left of us, but as we heard no whissing of balls, I [concluded] they were to Alarm the body that was there of our approach.” Off in the distance, militiamen could be seen hurrying into line. “The road before you go into Lexington is level for about 1000 yards . . . when we came up to the main body which appeared to me to Exceed 400 in and about the village who were drawn up in a plain opposite the church.”
Captain Parker’s men waited nervously for the arrival of the British regulars. As the troops approached, many began to realize the danger they were in. One was bold enough to tell Parker “There are so few of us! It is folly to stand here!” The militia captain, ignoring the outcry, turned to his company and stated “Let the troops pass by, and don't molest them, without they begin first.”
Pitcairn was confronted with a military quandary. If he chose to ignore the militia company drawn up on the village common, he would be leaving an armed opponent to his rear. If he halted, he could exacerbate an already tense situation
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