When Sir Henry Clinton's British troops reached Forts Clinton and Montgomery on October 6, 1777, some of his ships began moving upriver to support them. First came two galleys, the Dependence and the Crane, which were rowed into position. Four American ships, the frigate Montgomery, the sloop Camden, and the galleys Shark and Lady Washington defended the giant iron chain the Americans had stretched across the river below Fort Montgomery. As the British galleys approached, a fierce cannon battle ensued. The Dependence fired 95 shots from its 24-pounders and many more from its smaller 6-pounders, striking Fort Clinton and the American ships. The American commander held his fire until his ship, the Montgomery, was struck. He then returned the fire and ordered the massive 32-pounder cannon on board the Lady Washington to do the same. The guns from both forts fired on the British galleys too.
Just before the battle reached its climax, two larger British ships, the brig Diligent and the sloop tender Hotham, and another galley, the Spitfire, came into view. Sir Henry Clinton later wrote that the sight of these ships "crowding all sail to support" the attack convinced him to begin his final assault. At dusk, the British drove the Americans from the forts, and the American vessels turned to support their fleeing soldiers. The Montgomery saved many Americans from capture by using its cannons to keep the British from encircling the fort. The Shark, the Camden, and the Lady Washington were ordered to rescue as many Americans as possible. As night fell, the ships tried to escape upriver, but the winds were not strong enough to overcome the ebb tide carrying them downriver. The Camden was run aground by its crew and was captured by the British. The Montgomery and the Shark were burned by their crews before they could fall into enemy hands. Only the Lady Washington escaped upriver.