Historical Marker #1579 in Madison County commemorates the final destination point of Daniel Boone and his party of trail cutters. These men had taken a long journey during the months of March and April 1775, creating Boone Trace, which was the first road into what became Kentucky.

Boone's group arrived at Sycamore Hollow carrying member Felix Walker on a wooden litter between two horses. Walker had been seriously wounded in a Native American attack at the Twitty's Fort site on March 25.

As the party of horsemen approached their chosen destination, their attention was diverted by the thunderous sound of approximately two hundred fleeing buffalo. Felix Walker later wrote in his journal. "Such a sight some of us never saw before, nor perhaps may never again." As the men and horses approached, the entire herd forded the river and disappeared into the forest. At this point, the travelers surely must have realized—with relief and wonder—that they had reached the end of the trail and arrived at the objective which had seemed so distant and unattainable when they started the journey three weeks earlier.

Sycamore Hollow is near the mouth of Otter Creek on the Kentucky River. There, a grove of Sycamore trees flourished in the low lying area. The location was also the site of a salt lick, which probably attracted the buffalo that the party viewed upon their arrival. In addition, Sycamore Hollow is supplied with multiple springs, which made it prone to flooding.

On September 9, 1778, prior to the siege of Fort Boonesborough, Shawnee Indians under the leadership of Chief Blackfish, held a meeting under the shade of a large elm tree near Sycamore Hollow with Daniel Boone and a delegation from the fort. Chief Blackfish and the Shawnee wanted the white settlers to leave the area while the pioneers argued for their right to remain.

The summit ended in a violent physical confrontation when Indian marksmen hidden in the hollow began firing. Boone had posted settlers at the fort, and they returned fire. Blackfish and Boone grappled with each other, but eventually the Americans escaped back into the protection of the fort. Squire Boone, Daniel's brother, was shot in the foot but survived. The 1778 siege of Boonesborough lasted eight days until the Indians finally withdrew.

Fort Boonesborough's establishment and survival was subsequently consequential in the founding of Kentucky and the opening of the west.