Location: First on east side of US 23; five miles west of Wise. Second on South Fork of Pound; eight miles west of Pound. Third, at Flat Gap on North Fork of Pound.

Date: First 1794. Second about 1810. Third about 1825.

Description: See history.

History: Benjamin Bolling moved from North Carolina in 1794 and settled about two miles north of present town of Esserville, on state road 620. One son, Jeremiah, then a small boy, and his wife accompanied him here.
He lived here in a small cabin he built, for two years, when he sold his claim to another homeseeker and moved back to North Carolina. 
     In 1810, or thereabouts, Jeremiah Bolling was married to Sally Ward of Georgia, and remembering the Cumberland Mountains decided to seek hunting ground and a home in the wilderness. So he set out, accompanied by his father, then very aged, and established himself on a claim on the South (or Lick) Fork of
the Pound. Here two children were born and died and were buried on a hill back of the house in coffins hewn from poplar logs. Here he planted the first apple trees ever set out in Wise County. He had carried the scions across the mountains from North Carolina, in a gourd, which his father had used to carry powder in during his life as a soldier in the Revolution. This gourd is still in the possession of Benton Bolling, a great-great-grandson of the soldier, and great-grandson of Jeremiah. Here also, Jeremiah Bolling built a two room log house, intending to make it his home till death. But death caused him to change his mind. After the two first-born died, his wife was no longer satisfied there in sight of the little graves and he sold his claim here and moved across the dividing ridge and settled on the head of North Fork of Pound at present Flat Gap. Here he reared a large family, and here he died after a long life of struggle with the hardships of the wilderness.
     After he had established his home at Flat Gap he went far back on the slope of Pine Mountain and cleared up a small field and planted it in corn every year as long as he lived, but never made any attempt to harvest the crop. This field was planted to attract bear, deer and other game to the field where he would shoot
his supply of meat. This field, now grown up in undergrowth in a wild uninhabited part of Pine Mountain is known as the "Jerry Field." 

Source of Information: William Bolling, B. J. Bolling. Notes collected in my library.

The First Settlement of Benjamin Bolling
 

Location: Five miles southwest of Wise. On State Road 620. East side, fifty yards from highway. Three miles north of Esserville.

Date: 1794.

Owners: Settled by Benjamin Bolling. Sold by Bolling to an unknown settler. Surveyed by Alexander Gray. Major Harvey Gray 1880-1915. 
Daniel Joseph Bolling 1915-1937.

Description: Described by descendants of Benjamin Bolling as a small one-room round-pole cabin.

History: Benjamin Bolling came from North Carolina in 1794 and settled just south of the mouth of Rocky Fork of Guest River. While living here, Mrs. Bolling was attacked by a panther at the spring one morning and she fought the animal off with a piggin until her husband ran to her rescue and shot the panther. After living here about two years, Bolling sold his claim for a rifle gun and two hound pups and went back to North Carolina. Later he returned with his son, Jeremiah Bolling, and settled on the Pound.
 

The Bolling Powder Gourd
 

Location: On the Pound-Flat Gap Road. Three miles east of
Flat Gap at the home of Benton Bolling.

Date: About 1772.

Description: Ordinary yard or garden variety of gourd. About 10 inches across bottom (blossom end), flat, with handle (stem) cut off about three inches long, into which powder was poured or loaded into rifle. It is highly polished by age and is chocolate brown in color.
     
History: Benjamin Bolling was a soldier in the American Army of the Revolution. He prepared this gourd to carry his powder in so as to keep it dry. He prepared a deer skin bag or covering for the gourd to protect it from
breading, and this covering is still on it. When he made his second and final journey into what is now Wise County, to establish a home, he carried a few scions in this powder gourd tied to the horn of his saddle all the miles across the mountains from North Carolina to the head of the Lick Fork of Pound, where he used them to plant the first orchard in Wise County. That was about 125 years ago and some of the trees are still living and bear annual crops of fruit.
     On Benjamin Bolling's death in 1835, the gourd fell to his son Jeremiah Bolling. He faithfully preserved it until his death about 1860, when it became possessed by Amos Bolling, Jeremiah's son, and his son, John, fell heir to it and at his death in 1935, it came into the hands of his son, Benton Bolling.
     It has been used in recent years to store bean seed and other garden seed in.

Source of Information: Benton Bolling, William Bolling. Notes furnished me by the late William D. McNiel.