Dillion Asher was born around 1777 in North Carolina to William "Billy" Asher and Margaret "Peggy" Blevins. Peggy was a sister of Old Dillion Blevins, a longhunter. A story says that Dillion Asher's father drowned in the Holston River in 1789 while hunting when they were living at Bean Station, Tennessee. Dill was about twelve.

About 1792, Dill Asher and Dillion Blevins started for Boone's Fort by way of Straight Creek Red Bird River. Along the way, while stopping to rest, Dill planted some peach seeds in Clay County where Phillip's Fork and Red Bird Creek joined. The story says that they backtracked to avoid some Indians, and stopped at the home of Richard Davis who had a tavern near Cumberland Gap in present-day Middlesboro, Kentucky.

In 1795 Dillion became the first keeper of the toll gate at the Cumberland Ford of the Cumberland River. Cumberland Ford was on the Wilderness Road in present-day Pineville, Kentucky. Later, there was a dispute between Dillion and another man over land. The story says that Dillion was warned that the man was going to kill him. Dillion and his family left for the area where he had planted seeds all those years before.

Dillion and his family arrived at Red Bird Creek around 1799-1800 where it is said they found the peach trees that he had planted were in full bloom. He built a log home on what is now called Asher Branch on the waters of the upper Red Bird, near the peach tree orchard. There was only one other known resident in the area, John Gilbert.

Asher was on the grand jury the day that the first Clay County court was seated, April 13, 1807. He was a major player in the early development of the timber industry in Clay County. There are many stories and legends about Asher. It is said that Dillion Asher became friendly with Indians who lived in the area, and they wrestled and had matches at the mouth of Straight Creek. A legend says that he killed the last buffalo that was killed in Kentucky and that he killed it when there were hundreds of buffalo stampeding on Buffalo Hill at Red Bird.

Dillion Asher died May 8, 1844, at age 66 in Red Bird. He, and other members of his family, are buried in a small cemetery on a knoll just above his log cabin.

Dillion Asher established a large clan of Ashers in Clay and Leslie Counties. Dillion's cabin, which was built around 1799, is still there and is well-preserved. It is one of the oldest structures in Clay County. The cabin is located at the Red Bird Mission Hospital at the far southern end of Clay County on KY 66, an especially scenic drive that takes you from Oneida through the sparsely settled Red Bird Purchase Unit of the Daniel Boone Forest.