Gibson County was originally part of Knox County. It was organized as a separate county in 1813. The first settlers had arrived about 1790. Most of the early settlers came from the Carolinas, Tennessee, Kentucky, and Virginia. The settlement period extended to about 1850.

The land where the buildings of Kolb Homestead are located (except for one of the log structures, which is on the adjoining tract to the west) was part of an 80 acre tract purchased by Daniel Kirk from the U.S. government in 1822. Kirk died soon after, and the land was owned by his heirs until 1846, when it was sold to Caleb Trippett. At the time it was sold, 25 acres had been cleared, and the 80 acre tract was appraised at $400. Trippett already owned the adjoining 80 acres to the east, and approximately 60 acres to the west. He had been born in Gibson County in 1818. He married Mary Fentriss in 1846. It appears likely that the brick house was built shortly after. Tax records of 1856, the earliest available, indicate improvements valued at $920 on the land where the house is located. There were improvements on the property south of the house valued at $1,070. This second figure may, at least in part, represent a barn remembered by a former resident of the farm, Chester Kolb, who lived there from c.1904 to c.1918.

Trippett was a prominent Gibson County farmer, a livestock raiser, and grain and pork dealer. He was elected to the Indiana House of Representatives in 1857, and served as Gibson County Treasurer from 1864 to 1868. He was president of the Princeton Banking Company, the first bank in Gibson County, founded in 1869 and later reorganized as the Gibson County National Bank. The bank failed in 1874 as a result of the Panic of 1873. The subsequent economic depression of the 1870s had a devastating effect on Trippett. He owned several hundred acres of farmland, but was forced to sell much of it because of his inability to keep up with property taxes and mortgages. In 1880, he sold the property. It was acquired by Jesse and Jennie Glaze in 1883.

Jesse Glaze was born in Tennessee in 1836. Jennie Gray was born in 1848 in Pike County. They married in 1867. They lived on the farm from the time they purchased it in 1883 until about 1904, when they moved to Princeton. The farm was then rented to the Joseph Kolb family until about 1918. At some point, the farm was transferred to the Board of Ministerial Relief of the Cumberland Presbyterian Church, located in Patoka. In 1919, the farm, which by this time comprised approximately 300 acres, was sold to Thomas Duncan for $12,625.

Shortly after acquiring the farm, Duncan tore down a log and timber frame barn, a carriage shed, a chicken house, privy, and combination wash house/smoke house. He removed the upper story of the rear addition to the house. He built the two large barns which are southeast of the house, and a small, frame house, which is located south of the house. He retained a small, frame structure, built c.1900, which is thought to have served as a granary, located southwest of the house.

Duncan was born in Gibson County in 1860, and grew up on a farm in Barton Township. He attended Central Normal College in Danville and taught school for nine years. He married Leila Wise in 1884. In 1889, he passed the bar examination and became an attorney. Later he became a judge and was active in local politics. He did not farm the land himself, but rented it to at least four renters during the 20 years he owned it. After his death, his heirs sold the approximately 300 acre farm to the Louisville Joint Stock Land Bank for $11,253. In 1944, it was acquired by the Union National Bank of New Albany for $20,566.

Joseph Wilbur and Leotis Kolb, brothers of the family who had lived on the farm earlier in the century, bought it in 1945. About 1950, the Kolbs moved the timber frame barn, and the two log structures onto the farm. In 1954, Leotis sold his share to Wilbur. Wilbur Kolb died in 1990. His heirs continue to operate the farm.

The farm illustrates several stages of agricultural development in Gibson County. Most of the early settlers of the county were farmers. During the settlement period, farming was, for most, a subsistence occupation. The difficulty of clearing the land of virgin forests is illustrated by the fact that only 25 acres of the original 80 acre farm of Daniel Kirk had been cleared by the time it was sold in 1846. The brick house constructed by Caleb Trippett in about 1850 was a substantial one for its time. It appears likely that his family was relatively well off.

The Trippetts had been Gibson County pioneers, and had been acquiring land for several years. Part of Caleb's 160 acre farm had been a gift from his parents. The farm was several acres larger than the average size farm in Indiana of 136. Over the years, Trippett acquired other farms, and rose to a position of prominence among county farmers.

The Panic of 1873 started an economic depression that would affect everyone in the state. Farmers were particularly hard-hit. The depression was especially severe for farmers in the southern counties. These counties were already experiencing competition from central and northern counties, where the land was more favorable for agriculture, and transportation routes were more extensive. Through the seventies, the value of agricultural products continued to drop, making it difficult for many families to keep their farms.

By 1880, farm prices had started to rise again. The period between 1880 and about 1900) was generally one of innovations in farm practices, improvements in education, better markets, and a greater involvement by farmers in politics. The years between 1900 and 1920 were ones of unprecedented growth in farming. The prosperity was seen less in the southern counties, where farms were generally producing smaller yields, but the Glazes were apparently doing well, their farm consisting of rich, tile-drained river bottom land.

In the early part of the 19th century, most farms were farmed by their owners. In 1880, about 24 per cent of all Indiana farms were farmed by renters. By 1900, this figure had increased to about 29 per cent. When the Glazes rented their farm to the Kolbs in 1904, this had become a fairly common practice. During the first two decades of the 20th century, farm prices were high, and renters did well. By the time the Kolbs left the farm, in about 1918, they were able to buy their own farm and build a house.

Prosperous times may have given Thomas Duncan the confidence to make many improvements, discussed above, soon after he acquired the farm in 1919. A recession in farming, starting about 1920, and worsening during the depression years of the 1930s, probably kept Duncan from making much money on the venture. After his death, the farm was sold, in 1939, for $11,253, less than the $12,625 that it cost him to buy in 1919.

Rural resources of all types are becoming increasingly rare in Gibson County. During the settlement period, the population had grown at a steady rate, reaching 10,771 in 1850. In 1870, the population of 17,371 compared favorably to that of other counties in the state. In 1870, farming was still the most important occupation in Gibson County. As such, one would expect to find a fair amount of intact rural properties dating from the years before 1870. Only nine rural properties, however, including the Kolb Homestead House, dating from before 1870, were identified as outstanding in the Indiana Historic Sites and Structures Inventory.

Farming in Gibson County became more difficult with the depression of the 1870s, and competition from central and northern counties. Though the Kolb Homestead land was prospering, much of the farmland in Gibson County was submarginal. By 1870, coal mining was becoming increasingly important. For economic reasons, there would have been less of an incentive to invest in the maintenance of old farm buildings, or the construction of new ones.

A site on the north bank of the Patoka River, a popular gathering place in the early 20th century, is a representation of rural social life. People gathered here on Sundays to enjoy the site's beauty. Area children came to swim here. Part of the attraction for them was a wooden barge used to ferry farm equipment across the river. When the barge was not in use for this purpose, it could used as a diving board. In contrast to the surrounding clay soil, this river site was sandy. Chester Kolb relates that the sand was so fine, that people would often come to get it for making plaster.