Battle of Little Mountain The Battle of Little Mountain , also known as Estill ' s Defeat , was fought on March 22 , 1782 , near Mount Sterling in what is now Montgomery County , Kentucky . One of the bloodiest engagements of the Kentucky frontier , the battle has long been the subject of controversy resulting from the actions of one of Estill ' s officers , William Miller , who ordered a retreat leaving the rest of Estill ' s command to be overwhelmed by the attacking Wyandots . Background . On March 19 , 1782 , Captain James Estill received a message from Colonel Benjamin Logan requesting assistance after signs of a Wyandot war party had been seen near Boonesborough , also , empty canoes having been seen floating down the Kentucky River . Gathering about 40 men from nearby settlements , Estill began searching the area . While he was away , the Wyandots attacked a number of nearby settlements , including Estill ' s Station , killing 14 - year - old Jennie Glass and capturing Munk ( or Monk ) Estill , a slave who belonged to James Estill . Under interrogation , the courageous slave was able to persuade the Wyandots to hold off their attack , convincing them that Estill ' s Station was at full strength . ( In reality , with the exception of one man on the sick list , only women and children were present at the fort ) . After killing a number of cattle , the Wyandots fled across the river . As soon as the Indians retreated , Samuel South and Peter Hackett , both young men , were dispatched to find Captain Estill and inform him of the attacks . They found Estill near the mouth of Drowning Creek and Red River early on the morning of March 21 . About half of Estill ' s 40 men had left families at the fort . They returned to Estill ' s Station that same day . Estill soon returned with the rest . He ordered five men to remain at Estill ' s Station and led the others in pursuit of the Indian raiding party . He set up camp at Little Mountain , near present - day Mt . Sterling , Kentucky . Resuming the chase the next morning , Estill was forced to leave behind 10 more men whose horses were too tired to continue . Finding fresh tracks , Estill and the 25 men remaining soon overtook the Wyandots at Little Mountain Creek . Battle . On the night of March 22 , 1782 , Estill and his militiamen encountered the Wyandot raiding party . Separated by Little Mountain Creek , they were a mile and a half south of Little Mountain . The two sides fought in a violent , pitched battle for nearly two hours . The Wyandot leader , Sourehoowah , was reportedly shot by the first volley and urged his men to continue fighting as he lay dying . After firing at each other across the creek for some time , both sides had suffered heavy casualties . When the Wyandots began fording Little River Creek , Estill countered by dividing his forces into three groups . Estill took the right flank , the left being given to Lieutenant William Miller , while another officer held the center . Miller was ordered to flank the rear of the Wyandots from the left . As he prepared to lead his men into battle , a musket ball apparently hit his rifle , knocking the flint from the jaws of the lock . Miller allegedly shouted that " " it was foolhardy to stay and be shot down " " , and he fled the scene with his men following him . With Estill ' s left flank now open and the creek defended by only four men , the Wyandots easily rushed in , killing Estill and six others as the militiamen retreated . Estill had already been wounded three times . As he attempted to escape with his men , he was killed in hand - to - hand combat by a pursuing Wyandot warrior . Militiaman Joseph Proctor witnessed Estill ' s death and shot the attacker dead with his rifle . Only a handful of men were left on each side , and the battle ended with the Kentuckians withdrawing from the field . Those Kentuckians who had been captured later reported the Wyandots had suffered about 20 casualties . The slave Monk , who had escaped during the battle , reported that 17 Wyandots had been killed and two more wounded . This was confirmed by another prisoner who later escaped . Among the 18 Kentuckians who survived the battle at Little Mountain were frontiersman James Anderson , David Lynch and William Irving . Adam Caperton , the father of United States Congressman Hugh Caperton , was killed . Aftermath . William Miller became the scapegoat for both the Kentuckians ' defeat and the death of Captain Estill . One of the survivors , David Cook , reportedly threatened his life twenty years after the battle . Miller never returned to Estill ' s Station to defend himself against his accusers . Monk Estill won particular distinction for bravery during the battle and carried a wounded militiaman , James Berry , almost back to Estill ' s Station . He was granted his freedom soon afterwards by Wallace Estill , becoming the first slave to be freed in Kentucky . The last survivor of the battle , Joseph Proctor , died at his home in Irvine , Kentucky , on December 2 , 1844 . He was 90 years old . The traditional site of Estill ' s death , where he was killed in hand - to - hand combat , is marked by a millstone marker pointing to an old sycamore tree on Kingston Creek . In 1808 , Estill County , Kentucky , was named for Captain James Estill .