On October 28, 1776, the Continental Army had marched north of Manhattan, withdrawing to the hills of the village of White Plains. Since the Battle of Brooklyn, General Howe had been pursuing the Continental Army in an attempt to encircle and destroy it. Although the Americans were not winning, their losses were actually helping the army steadily improve. The Battle of White Plains, which occurred on October 28, 1776, demonstrated the progress that the Continental Army had made since the Battle of Brooklyn in August.
Similar to Long Island, the Maryland Regiment would play a key role at the Battle of White Plains. This time Smallwood’s men fought alongside troops from Delaware, New York, and Connecticut. They were positioned apart from the rest of the Continental Army, on Chatterton’s Hill, a rocky ridge about 180 feet high. Its height made Chatterton’s Hill a smart defensive post– a Hessian officer would write later that the Americans had “excellent positions at White Plains.”
At ten o’clock, Howe’s army approached the American lines; that morning approximately 13,000 men marched across the field below. The British bombarded the Americans with a “heavy cannonade.” The men on the ridge could only reply with their two cannons. Colonel Smallwood and his regulars were ordered to descend the hill and attack, initially driving the enemy back until the British rallied and, according to a Marylander at the battle, the enemy gained the advantage by attacking the right of the brigade, which was composed of Connecticut militiamen.
For another half an hour the battle continued, and “Ritzema’s 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.” The British captured the hill. Although the Americans had again been overwhelmed and driven from the battlefield, the retreat was orderly, in contrast to the desperate escape at Long Island. According to our letter writer, Colonel Smallwood withdrew particularly reluctantly, arriving back at camp at around three o’clock. During the retreat he was wounded through his hip and his arm, although neither injury was life threatening. 
However, not all of the officers of the Maryland Line survived the battle; all together, approximately forty men from the Maryland Line were killed, captured, or wounded. The Regiment had 298 men fit for duty after the battle. Two of those killed were Captain John Day Scott, a veteran of the Battle of Brooklyn, and Captain Bennett Bracco of the First Independent Company. Of the men who we know participated in the Battle of Brooklyn, Lieutenant Thomas Goldsmith’s leg was badly wounded. Private John Hughes was injured by a cannonball in a related skirmish and Private William Marr was wounded and sent to a hospital in North Castle, New York. John Babbs, another private, had his “leg badly broken by a piece or fragment of a rock knocked off by a cannon ball.” 
All of the regiments present at White Plains took heavy losses– a single Hessian volley wounded and killed ninety-two men. However, victory came at a high price for the British, and one unofficial tally counted more than 349 soldiers killed and wounded. After the Battle of White Plains, Major Mordecai Gist took command of the First Maryland Regiment as Colonel Smallwood recovered from his wounds. Gist wrote back to Annapolis that the British were building a breast work on the captured hill, and Washington ordered his army to abandon their front lines. The Continental Army would continue withdrawing to the north, and Howe would soon give up the chase and turn his attention to the isolated defenders of Fort Washington in Manhattan. The Battle of White Plains took place almost exactly two months after the Battle of Brooklyn, and the soldiers who had been part of the Maryland 400, along with those who served alongside them, continued to be among Washington’s most reliable and disciplined troops.
 David Hackett Fisher, Washington’s Crossing, (Oxford University Press, 2004), 111.
 Fisher, 110.
 Pension of John Babbs. National Archives, Revolutionary War Pension and Bounty Land-Warrant Application Files, S 45241, from fold3.com.