MSA SC 3520-17818
Robert Westbay enlisted as a sergeant in the Eighth Company of the First Maryland Regiment on January 23, 1776, during the Revolutionary War's earliest days. 
The regiment that Westbay joined was the state's first contingent of full-time, professional soldiers raised to be part of the Continental Army. As a sergeant, Westbay was responsible for keeping the soldiers of the company properly aligned during marches and in battle, and ensuring order among the men in camp, as well as other administrative duties. The Eighth Company, commanded by Captain Samuel Smith, formed in Baltimore in early 1776, and it trained there that spring and summer. Two other companies from the regiment were located in Baltimore as well, while the rest were stationed in Annapolis. In July, the regiment was ordered to march north to New York, to protect the city from invasion by the British. The Eighth Company lost four men who deserted along the march, a problem which plagued the regiment that summer. 
On August 27, 1776, the Americans faced the British Army at the Battle of Brooklyn (sometimes called the Battle of Long Island), the first full-scale engagement of the war. The battle was a rout: the British were able to sneak around the American lines, and the outflanked Americans fled in disarray. As the Maryland troops fought their way towards the American fortifications, they were forced to stop at the swampy Gowanus Creek. Half the regiment, including the Eighth, was able to cross the creek and escape the battle. However, the rest were unable to do so before they were attacked by the British. Facing down a much larger, better-trained force, this group of soldiers, today called the "Maryland 400," mounted a series of daring charges. They held the British at bay for some time before being overrun, at the cost of many lives, losing 256 men killed or captured. 
Because the Eighth Company was able to escape the battle early, it lost only about six men. Still, as its captain Samuel Smith later described, the retreat was not easy. While withdrawing, "the Regiment mounted a hill, [and] a British officer appeared…and waved his hat, and it was supposed that he meant to surrender. He clapped his hands three times, on which signal his company rose and gave a heavy [fire]. I took my company through a marsh, until we were stopped by the dam of a…mill…that was too deep for the men to ford. I and a Sergeant swam over and got two slabs [of wood] into the water, on…which we ferried over all who could not swim." Westbay was among the men who escaped the battle. 
In the weeks after the Battle of Brooklyn, the Americans were gradually pushed out of New York by the British. On October 28, the Americans marched out of Manhattan to White Plains, to take on a force of several thousand British soldiers. The Marylanders were positioned with men from Delaware and Connecticut on the top of a hill, in a strong defensive position. As the battle progressed, they were ordered to descend the hill to engage the British. They were able to push the British back for a time, but were eventually overcome when the British counterattacked and overran the Connecticut troops. The Maryland and Delaware soldiers stood their ground resolutely, and one observer noted that "Ritzema’s [the Deleware commander] and Smallwood’s [regiments] suffered most, on this occasion, sustaining, with great patience and coolness, a long and heavy fire–and finally retreated with great sullenness, being obliged to give way to a superior force." Though the Americans did not win a clear-cut victory that day, they nevertheless showed themselves to be the British's equal. 
However, the Maryland Line took heavy losses, just as they had at Brooklyn. Of the 298 men who were present at the battle, 46 were killed or wounded, 15 percent of the Marylanders' total men. The dead included many survivors of the Battle of Brooklyn, including John Day Scott, captain of the Seventh Company, and his lieutenant Thomas Goldsmith. The men lost at White Plains also included Robert Westbay. His captain Samuel Smith recalled that during a British artillery barrage, "a cannon ball struck the ground, and, in its rebound, took off the head of Sergeant Westlay [sic], over the shoulder of Captain Smith." 
The losses at White Plains were due in part to the Americans' tactical decisions during the battle. Lieutenant William Harrison, commander of Maryland's Seventh Independent Company, which had taken catastrophic losses at Brooklyn, wrote that, at White Plains, "our Generals showed not equal judgmental to that of the Enemy. We were badly disposed to receive an attack of the Enemy's small arms, and unfortunately much exposed to their Artillery, which flanked us so heavily as to render [our position] tenable [for] but a short time." Because the Marylanders were left exposed to such heavy fire, they took the brunt of the British attack. 
Because Westbay died so early in the war, and was likely a very young man, nothing else can be learned about his life before he enlisted in the First Maryland Regiment and fought as part of the famed "Maryland 400." Still, though he served only a short time, he evidently left an impression with his fellow soldiers. Caspar Clutter, a private in Westbay's company, still remembered serving under "Sergeant Wisby," as he called him, more than fifty years later. 
Owen Lourie, 2018; Additional research by Benjamin Flood, Washington College.
1. Muster Rolls and Other Records of Service of Maryland Troops in the American Revolution, Archives of Maryland Online, vol. 18, p. 18; Compiled Service Records of Soldiers Who Served in the American Army During the Revolutionary War, NARA M881, from Fold3.com.
2. Frederick Steuben, Regulations for the Order and Discipline of the Troops of the United States, Part I. (Philadelphia: Styner and Cist, 1792), 148-151; "Eight Pounds Reward." Philadelphia Evening Post, 10 August 1776; William Sands to John and Ann Sands, 14 August 1776, Maryland State Archives, Special Collections, Dowsett Collection of Sands Family Papers [MSA SC 2095-1-18, 00/20/05/28].
3. Mark Andrew Tacyn, "'To the End:' The First Maryland Regiment and the American Revolution" (PhD diss., University of Maryland College Park, 1999), 48-73. For more on the experience of the Marylanders at the Battle of Brooklyn, see "In Their Own Words," on the Maryland State Archives research blog, Finding the Maryland 400.
4. Return of the Maryland troops, 13 September 1776, Revolutionary War Rolls, NARA M246, folder 35, p. 85, from Fold3.com; “The Papers of General Samuel Smith. The General’s Autobiography. From the Original Manuscripts.” The Historical Magazine, 2nd ser., vol. 8, no. 2 (1870): 82-92. Smith wrote his autobiography in the third person; it has been converted to first person here for purposes of clarity.
5. Estimate of British strength run from 4,000 to 7,500 men. David Hackett Fisher, Washington’s Crossing, (Oxford University Press, 2004), 110-111; “Extract of another letter, dated in the evening of the above day,” Maryland Gazette, 7 November 1776; "Extract of a letter from White-Plains," 28 October 1776. American Archives Online, series 5, vol. 2, p. 1271.
6. “Extract of another letter"; "Extract of a letter from White-Plains"; Journal and Correspondence of the Maryland Council of Safety, 1776, Archives of Maryland Online, vol. 12, p. 418; Smith autobiography, 83.
7. Archives of Maryland Online, vol. 12, p. 488; "Doubts and Defeats: The Continental Army in 1776," Finding the Maryland 400 research blog.
8. Pension of Gaspar [Caspar] Clutter. National Archives, Revolutionary War Pension and Bounty Land-Warrant Application Files, S 5010, from Fold3.com.
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