14th Continental Regiment

On July 11, 1776, Glover was ordered to rejoin the main army in New York. The unit arrived in Manhattan on August 3, but was not ordered onto Long Island until August 28, after the Battle of Long Island. The unit took a position on the Brooklyn defense perimeter between Fort Putnam and Wallabout Bay where they immediately faced intense skirmishing into the night.[9] On the following day, Washington made the decision to evacuate his troops, and that evening under stormy conditions, ordered Glover and the 14th Continental to ferry the entire army across the mile-wide East River. On the morning on the August 30 under cover of fog, Glover and his men completed the task of moving the troops, horses, artillery and supplies across to Manhattan without the loss of a single life and without detection by the enemy.[10]

In early September 1776, Washington intended to use Glover's men in another amphibious operation to remove the sick, wounded and additional military supplies from Manhattan. A call went out to the New York legislature to send four Albany Sloops for the purpose, but these never arrived.[11] Whether or not the 14th Continental ultimately participated in the removal of the casualties is disputed.[12][13] On September 4, Washington put Glover in charge of a brigade that included the 14th Continental in a division commanded by General Israel Putnam. On September 14, Glover's brigade marched to Harlem to rejoin the main army. On September 15, the British landed on Manhattan at Kip's Bay, which led to a panic-stricken retreat by the American troops defending the shore, including two brigades sent to reinforce them. Despite Washington's best efforts to stop the retreat, they fled towards Kingsbridge until they met six brigades including Glover's that had been marched down from Harlem. Glover brought the troops into a line on a hill to meet the British, but Washington later ordered the troops to fall back.[14][15][16]

On October 14, 1776, Washington ordered the 14th and three other Massachusetts Regiments under Glover to Pell's Point to guard against a potential enemy landing. On October 18, while Washington was withdrawing the remainder of his troops to White Plains, General William Howe ordered an amphibious landing at Pell's Point. What ensued came to be known as the Battle of Pell's Point; it was a significant strategic victory under Glover, although it appears that he held the 14th in reserve and they did not participate directly in the battle.[17] As Washington's army fell back to White Plains, Glover's men continued to harass the enemy. On October 20, Glover's brigade launched a raid behind enemy lines to bring back 200 barrels of pork and flour that had been left in Eastchester. Several days later a scouting patrol from the 14th Regiment unexpectedly ran into a party of Hessians, killing twelve and taking three prisoner.[18] Glover's men also participated in the Battle of White Plains, principally as part of the artillery engagement and later as the rear guard as Washington moved on to New Jersey. Glover's brigade left White Plains to rejoin the rest of the army on November 22.

As the end of 1776 approached, Washington faced a desperate situation. Morale was low, and the enlistments for many of his regiments, including the 14th, were set to expire at the end of the year. Washington decided to get one more battle in before these troops left the service. Howe had pursued Washington through New Jersey, but as Washington crossed the Delaware River into Pennsylvania, his troops had collected all the boats they could find, effectively preventing Howe's further advance. Howe halted his campaign for the winter, moving most of his army back to New York, but leaving a chain of garrisons behind to hold New Jersey. Washington devised a plan to attack the garrison at Trenton, and selected Glover and the 14th Regiment to ferry his troops across the Delaware. The 14th were provided a number of Durham boats for the task, averaging 60 feet (18 m) in length with an 8 feet (2.4 m) beam, each capable of holding an entire regiment. The boats were propelled by oars measuring 18 feet (5.5 m) on the downstream side and poles on the upstream side.[19] Washington ordered the operation for the night of December 25–26, which turned out to be a howling snow storm. As the 14th ferried the heavily laden boats across, they had to contend with ice forming on the gear, and cakes of ice that needed to be wrestled out of the way.[20] In addition to ferrying the troops, the 14th was responsible for ferrying the artillery that was under the command of Colonel Henry Knox. At 3am on the morning of December 26, three hours behind schedule, the 14th Regiment completed their task.

After the crossing of the Delaware was completed, the 14th Regiment joined the other regiments in Glover's brigade in General John Sullivan's division and were part of the American victory at the Battle of Trenton that immediately followed. The 14th Regiment then assisted in they ferrying of Washington's force and approximately 900 Hessian prisoners back across the Delaware.[21]