The year was 1775 and as the sounds war grew louder, the men of the Emmitsburg area quickly answered the call for troops, forming two companies: the Game Cock Company under the command of Captain William Blair, and another company under the command of Captain William Shields. These companies were manned by more than a hundred soldiers that were ready for military use. 

These companies were mustered into service with the Maryland Militia, also known as the Maryland 400 or Smallwood’s Battalion. The Smallwood’s Battalion of 4,000 troops was formed into five companies, including the two companies from Emmitsburg. The Maryland 400 hurried North into New York in July of 1776 to join the American army under the command of the great General George Washington. The Maryland 400 would gain their heroic reputation by turning the tide of the Revolutionary War at the Battle of Long Island.

General George Washington wanted to seize New York after the British abandoned Boston in March of 1776. He saw that the British would soon invade the New York area as a tactical offence, this would possibly result in a decisive victory for the British. This could lead to many colonists turning away from joining the patriot’s cause for independence. In the spring of 1776, General Washington removed his army from Boston and headed toward New York. In the latter part of June, as the American troops retreated from Canada, British vessels entered New York Harbor. As the month of July drew to a close, the British had already taken Staten Island and were blockading the lower half of the harbor. Approximately three hundred ships of supplies and transports dotted the ocean near Staten Island. By August the Maryland 400 had engaged in their first major battle of the Revolutionary War at Long Island.

Washington's Continental Army was outnumbered, outgunned, out-supplied and they were not ready to face a well disciplined British army of about 27,000. General Washington reported that he had about 30,000 men, but only 20,000 could be used for military duty. The men in the American army did not compare to the military experience of the British. General Washington had to engage the British, or the efforts of the War for Independence would be lost. 

The Maryland 400, along with the rest of the army, fortified their positions and began to lay siege to New York. General Washington expected to lead his army in a two pronged attack with Manhattan, this was his primary objective. He sent roughly eighteen hundred troops across the East River to Brooklyn Heights as part of his strategy. The Long Island attack was the beginning of a large-scale onslaught on Manhattan. General Howe landed his 20,000 troops near Brooklyn on August 22, 1776. With this intelligence General Washington was convinced that the main British force would concentrate on Brooklyn Heights.

General Washington ordered 10,000 troops under the command of General Israel Putnam to be deployed at Long Island. The Maryland 400 under Major Mordecai Gist supported the right flank of the Continental Army. On August 27, 1776 the British sent two divisions to engage Sullivans’ and Stirling's brigades, while General Howe moved his men through the night to encase Sullivan's left flank. In the early morning hours Hessian soldiers maneuvered through the key passes in the center of Sullivan's and Stirling's brigades. General Howe's troops concealed all flanking activity. The Jamaica Pass was virtually defenseless. 

The British Army was now in a position to attack. At 8:30 a.m., General Howe issued orders to his men to storm the rear of the American center and left flank. Sullivan turned to meet the British, but the unanticipated attack caused confusion as Hessian soldiers broke through the American center behind them. This led to the collapse and retreat of Sullivan's entire left wing. On the right flank of the American army the Maryland 400 quickly moved in and took up defensive positions on Haslet's Delaware's left side. American patriots saw a red line appear before them and the exchange of musket fire began to dominate the battlefield. The troops of the Maryland 400 were on the defense until 11 am, as Stirling's troops defended each and every British attack.

While the British were re-supplied and reinforced to 9,000 men, the strength of the Americans began to dissolve. General Howe launched an assault against the Marylander’s right flank applying intense pressure upon them. Stirling realized that his 950 men could not hold the British flanking movement on his right. He realized that his men were in danger of being completely shut off from the only remaining path of retreat. The Gowanus Salt Marsh was important to the Americans because it represented the only retreat back to their primary positions in Brooklyn Heights. Stirling and his men retreated toward the Mill Dam road and bridge which were the only solid ground over the swamp.

As the right flank of the American army retreated, Stirling realized that another British force was fast approaching his left wing near the Cortelyou House. Stirling immediately detached half of the Maryland 400 and ordered his Delaware troops and remaining Marylanders to retire across the swamp. Major Gist and his 250 Marylanders were ordered to engage the British at the Cortelyou House in a heroic attempt to hold the British while the rest of Stirling’s command departed. The British met them with a devastating volley of musket fire. The Marylander’s halted, fell back, reformed and advanced toward the house again. 

The British musket fire cut threw the Marylanders, forcing them to retreat and reorganize once again. The British inflicted heavy casualties on the Marylander’s, as they assembled for three more gallant but barren assaults. As the Marylander’s reorganized for their last attack, they were battered by the British reinforcements that had arrived on the battlefield. The survivors retreated and desperately pursued a way back to their army. With the British taking possession of the Cortelyou House, the Marylander’s were denied their route of retreat at the Dam Road crossing. Disposing of their weapons and provisions, the retreating army struggled through the marsh and swamp. 

Their retreat was overlooked by General Washington who was part of the Brooklyn defenses. Smallwood brought up two light artillery pieces and some rifle soldiers to discourage the pursuing British as they came up from the far side of the swamp. Smallwood’s quick actions allowed the remaining Americans time to swim their way to safety. By two o'clock in the afternoon the battle of Brooklyn Heights was over. Stirling and Major Gist had been captured and only 10 out of the 250 Marylanders had returned from this gallant counterattack.

The battle of Brooklyn Heights turned out to be a stinging loss for the Americans. More than a thousand men were killed, captured, or missing. Generals Stirling and Sullivan were captured by the British and the battalion itself lost more than 250 men. The majority of the casualties for the Marylanders occurred during their retreat and their desperate, but none the less, heroic action at the Cortelyou House. Of the original Maryland 400, only 96 returned, and out of those 96 only 35 were fit for continuing duty. Although the Maryland 400 was almost destroyed, the survivors would still fight at the battle of White Plains, New York.

The battle of White Plains, New York was fought on October 28, 1776. The forces of battle included approximately 2,000 Americans, under the command of General George Washington, and 13,000 British and Hessian troops led by the British commander in chief, Sir William Howe. While General Washington retreated from the battle of Brooklyn Heights, the Continental Army had repulsed a British advance at Harlem Heights on October 16. General Washington then withdrew his army to White Plains, New York on October 21. The Americans fortified Chatterton Hill on the west bank of the Bronx River, in the vicinity of White Plains and prepared to face the oncoming British army.

General Howe landed 4,000 troops at Throg's Neck on October 12. British intentions were to encircle Washington's army and bring the revolt to an early end. Upon landing the British were confronted by Colonel Ed Hand's Pennsylvania riflemen who destroyed the bridge and embankment leading from Throg's Neck to the Westchester mainland. General Howe's men were battered for six days before they reassembled and landed at Pell's Point in Pelham Manor on October 18. Colonel John Glover and his diluted brigade of Marblehead troops remained on the right of Washington's northerly movement. Their assignment was to protect the Boston and White Plains Post Roads. Colonel Glover placed his regiments in a succession of ambush points along the route of Howe's army. The ensuing enfilade and leapfrog ambush tactics triggered by Glover's daring headlong charge decimated the British and Hessian advance guard. The skirmish at Pelham was the opening act for the battle of White Plains.

General Washington combined his forces in Ft. Washington and Kings Bridge and moved north toward White Plains along the Albany Route. The rear of Washington’s army was brought up by General Charles Lee's Virginia Division. Loaded with equipment and supplies, they started out on October 18, traveling on the west side of the Bronx River. On October 21, parts of Washington’s army began fortifying Chatterton, Purdy, Merritt, Hatfield and Miller Hills. Occasional skirmishes broke out across the Bronx River as rival forces exchanged shots with the patriots. On October 26, the rear of Washington’s army reached White Plains.

October 28, was the opening day of the Battle of White Plains. During the morning General Howe deployed a third of his army and began a powerful frontal and flank assault on the American troops at Chatterton Hill. His battle plan called for a tactical offensive attack of Chatterton Hill. Phase one was led by Lt. Gen. DeHeister, who commanded the Hessians and moved westward down Mamaroneck Road to Post Road. It continued ventilating out through Scarsdale mainly in Greenacres, and into parts of Fox Meadow. The Hessians were advancing from Fenimore Road, which was no more than a towpath leading toward Hartsdale and Greenburgh. 

General Washington directed Maj. Gen. Joseph Spencer and 2,500 troops to engage the Hessians approaching from Chatterton Hill. The colonials moved across the Bronx River and engaged the Hessian troops, who then fell back into a retreat. Greenacres became the high tide of the battle. Colonel Ralle and his mounted Hessian dragons rode out in superior numbers and engaged General Spencer at Greenacres. Spencer was overrun and his line then gave way. The Americans fled to the other side of the Bronx River with the Dragoons close behind them. Once they reached Chatterton Hill, the Americans took cover from the fortifications that had been built. During the engagements with the Americans the British were thrown back during the assaults of Chatterton Hill. The Hessian dragoons eventually charged their horses up the hill and won the day for the British.

General Howe's delay, heavy rains that had fallen that day and battle plans that were not properly executed turned the tide of a British victory into a defeat of sorts. As the British began to defeat the American troops, General Howe’s flawless plan of encircling the Continental Army and ending the revolt early concluded disastrously as General Washington and his army retreated into New Jersey. With this retreat, General Howe assumed that the battle was over and sent the majority of his soldiers back to New York. Once the British returned to New York, General Howe proceeded to attack Fort Washington. He regained control of the fort and New York City. General Howe turned control of the British army over to General Cornwallis, who forced Washington’s army to cross the Delaware River into Pennsylvania.

The Maryland 400's reputation for their heroic counter attack against the British at the battle of Long Island still stands today. The Maryland 400 is still recognized as the State's primary endowment in the struggle for independence. General Washington recognized the gallant performance and included the men from Maryland in his rear guard to cover the astonishing evacuation of the American force in Manhattan on the night of the August 29. The significance of the Maryland 400's struggle at New York during the Battle of Long Island is impossible to calculate. General Washington complimented the troops from Emmitsburg at Tera Ruba near Tom’s Creek, saying that they will always hold a part of his heart for their courageous stand against the British during what was truly an inestimable moment in our American history.