Merritt Hill was the site of one of the actions in the Battle of White Plains on October 28, 1776. During the attack on Chatterton Hill, the British marched up the road to Connecticut, Lake Street, to attack the left flank of Washington’s defense assembled on Hatfield Hill opposite Merritt Hill. General Heath, under General Washington, had placed Colonel Malcolm, his New York Regiment, and Lieutenant Fenno with one field piece on Merritt Hill in defense of Hatfield Hill. Lieutenant Fenno fired a cannonball directly into 20 British horsemen approaching Hatfield Hill, and this single shot caused the British to retreat back toward White Plains.