The settlement had a fort containing 300 soldiers, and even though spies had reported that the enemy force was moving towards Cherry Valley, Ichabod Alden, the fort's Colonel, failed to take precautions to defend the fort. The enemy force arrived near Cherry Valley on November 10th, and did some reconnaissance on the settlement and identified weaknesses in Alden's arrangements and the raiders decided to send two seperate forces out. One to attack Alden's headquarters (located about 400 yards from the fort in a house owned by the Wells family) and one to attack the fort itself. During the final meeting before the raid, Butler made the Indians promise that they would not harm noncombatants.
The attack began in the early morning on November 11th, though they tried to remain stealthy, a few Indians opened fire on some settlers chopping wood, one was able to escaped and raised the alarm. The raiders then split up with a group of Senecas led by a Seneca Chief called Little Beard surrounding the house where Alden was holed up and the main body surrounding the fort. During the resulting volley, the raiders killed around sixteen officers, including Alden, who eyewitness reports say was running from the house to the fort as he was cut down. The raiders also took the fort's second-in-command, Lieutenant Colonel William Stacy prisoner. The entire Wells household was killed after raiders gained entry into the home.
After failing to take the fort, having lacked the heavy firepower needed to do so, the Indians ransacked the settlement, burning every house in the settlement. Leading this charge were the Senecas, spurred on by revenge for the ransacking of their own settlements. They slaughtered anyone they came across, despite Butler and Brants orders. When the raid was over, 14 soldiers (including Alden) and and 30 civilians were dead and several others were taken prisoner.
Taking the attack to heart, the Continental Army soon launched the Sullivan Expedition, which resulted in over forty Iroquois villages being destroyed, but the expedition did nothing in stopping the Frontier War.