It is believed that N. J. Thompson was the first actual settler in what is now Cowley county. He built a cabin on the Walnut river, near what he supposed was the south line of Butler county, in Aug., 1868, but it was afterward found that he located in Cowley county. The land was still an Indian reservation, but the white settlers were attracted by the fertility of the soil and another settlement was soon made south of Thompson by William Quimby and a man named Sales. Cattle dealers began to come among the Osages to purchase their herds and carried back reports of the rich lands, which caused a number of white settlers to trespass on the Indian reserve and make settlements.

Among those who came in 1869 were James Renfro, T. B. Ross. John and Joseph Stanbury, F. W. Schwantes, S. B. Williams, B. F. Murphy, T. A. Blanchard and some others, extending the settlements southward to within 4 miles north of the present city of Winfield. In June, 1869, C. M. Wood brought a small stock of groceries from Chase county to sell to the Indians. This stock he kept at Renfro's house for a time, but soon erected a stockade and cabin on the west bank of the Walnut nearly opposite where Winfield now stands. The Indians were numerous and knowing the insecurity of the whites in the country, began to steal and make unfriendly demonstrations, which caused Wood to move back to Renfro's for safety.

About the same time that Wood came, E. C. Manning and P. Y. Becker came down the valley and erected a cabin for the latter at the bend of the Walnut river about 2 miles below Winfield, and on June 11 Manning laid claim to the land where a part of Winfield now stands. In August all the settlers in the valley were ordered off the Indian lands. Wood's stockade was burned and all the settlers but T. B. Ross left for Butler county. Later the settlers began to drift back, and in September several families came down the valley to settle near Manning.

These settlers each paid the Osage chief $5 for the privilege of remaining. Among them were W. G. Graham and family, Mrs. Graham being the first white woman of north Timber creek. Prettyman Knowles, James H. Land and J. C. Mountfort also located in this neighborhood. In December Alonzo Howland, W. W. Andrews, Joel Mack, H. C. Loomis, A. Mentor and others took up claims. Mr. Howland built a dwelling on his land just south of where Winfield now stands, which was the first frame house in the county, the lumber for it having been hauled 100 miles.

During the summer of 1869 H. C. Endicott, Edward Chapin, George Harmon, W. Johnson, Patrick Sommers and others took up claims as far south as the site of Arkansas City. In June, 1870, a party of men took claims along the Grouse valley, among whom were John Nichols, O. J. Phenis, D. T. Walters, Gilbert Branson and William Coats. Up to this time all settlers had been trespassing on the Indian lands, but on July 15, 1870, the Osage diminished reserve was opened for settlement and the whites began to pour into the county. The land was surveyed and sold to actual settlers in quantities not exceeding 160 acres each. Among the new arrivals were J. C. Fuller and D. A. Mulligan, who bought A. A. Jackson's claim which adjoined Manning's. Max Shoeb built a log blacksmith shop, and W. Z. Mansfield opened a drug store in a log cabin, the first of its kind in Winfield.

The first newspaper of the county was the Cowley County Censor, owned and edited by A. J. Patrick, the first issue being dated Aug. 31, 1870. The first postmaster in the county was C. H. Norton of Arkansas City, who was appointed on April 18, 1870. The next was E. C. Manning at Winfield, who was appointed in May. The first United States census was taken in June, 1870, and the population at the time was 726. The first session of the district court was held at Winfield on May 23, 1871, by Henry G. Webb, judge of the Eleventh judicial district. Arkansas City and Winfield were hardly established as towns before schools were opened. In 1871 a $10,000 school house was built at the latter place and the same year thirty-seven districts were organized, although only three erected buildings. The Methodists were the pioneer religious organization in the county. They perfected a church organization at Winfield in the spring of 1870 under the direction of B. C. Swartz, and in the fall the Baptists organized a church at Winfield. These were followed soon by other denominations.

Early in Feb., 1870, a bill was introduced in the legislature to organize Cowley county. This bill named Cresswell (now Arkansas City) as the county seat. The citizens of Winfield determined to have their town made the county seat. C. M. Wood, A. A. Jackson and J. H. Land made a canvass of the county and found that it contained over the necessary 600 inhabitants for organization. Papers were made out and forwarded to the governor, petitioning him to have Winfield made the seat of justice. On Feb. 28, 1870, the governor proclaimed the county organized, with Winfield the temporary county seat.

On Aug. 22, 1871, a petition was circulated to change the county seat to Tisdale, which was located at the exact geographical center of the county, but the vote resulted in a victory for Winfield. In 1873, the county buildings were erected, consisting of a court-house and jail. The former, which cost $11,500, was located on a block of land, one-half of which was donated to the county by the town company and the other half purchased by the commissioners.

The general surface of the county is gently rolling prairie. There are some bluffs in the east, and the western part is quite level. The valley of the Arkansas averages about 5 miles in width; the valley of the Walnut averages about 2 miles and the smaller streams from a quarter of a mile to a mile. Timber belts are found along the streams that vary from a quarter of a mile to a mile in width and contain Cottonwood, elm, hackberry, mulberry, walnut, oak, redbud, pecan, hickory, ash and cedar. The county is well watered by the Arkansas river which crosses the southwestern portion, and the Walnut river, which flows south in the western part of the county, and their tributaries, the most important of which are the Muddy, Dutch, Timber, Silver and Grouse creeks. Cowley county is one of the first counties in the state in the production of corn. Oats, winter wheat and other grains are also extensively raised. Live stock raising is one of the leading industries, and dairying is a paying business. There are about 300,000 bearing fruit trees in the county that bring in a large income. Magnesium limestone of an excellent quality is found and extensively quarried, both for local use and shipment out of the county. Gypsum is found in large quantities in the west. A large salt marsh exists in the southwestern portion.

Few counties in the state have better transportation facilities. Five lines of the Atchison, Topeka & Santa Fe railway system center at Winfield; the Missouri Pacific enters the county near the southeast corner and runs west to Winfield; a branch of the same system runs from Dexter to Arkansas City; the St. Louis & San Francisco crosses the county diagonally from northeast to southwest, through Winfield, and a line of the Kansas Southwestern runs west from Arkansas City. Altogether, the county has over 200 miles of main track railroad.

The population, according to the U. S. census for 1910, was 31,790. The value of farm products, including animals slaughtered or sold for slaughter, was $4,321,090. The five leading crops, in the order of value, were: corn, $674,865; hay, $581,383; oats, $398,559; Kafir corn, $172,500; sorghum, $101,760. Dairy products to the value of $429,123 were sold during the year.

Geography
According to the U.S. Census Bureau, the county has a total area of 2,933 km² (1,133 mi²), of which 2,917 km² (1,126 mi²) is land and 16 km² (6 mi²), or 0.56%, is water

Demographics
Cowley County's population was estimated to be 35,298 in the year 2005, a decrease of 982, or -2.7%, over the previous five years.

As of the U.S. Census in 2000, there were 36,291 people, 14,039 households, and 9,616 families residing in the county. The population density was 12/km² (32/mi²). There were 15,673 housing units at an average density of 5/km² (14/mi²). The racial makeup of the county was 90.13% White, 2.70% Black or African American, 1.96% Native American, 1.53% Asian, 0.01% Pacific Islander, 1.36% from other races, and 2.30% from two or more races. Hispanic or Latino of any race were 3.59% of the population.

There were 14,039 households out of which 32.20% had children under the age of 18 living with them, 55.20% were married couples living together, 9.60% had a female householder with no husband present, and 31.50% were non-families. 27.90% of all households were made up of individuals and 13.20% had someone living alone who was 65 years of age or older. The average household size was 2.46 and the average family size was 3.00.

In the county the population was spread out with 26.00% under the age of 18, 9.90% from 18 to 24, 26.00% from 25 to 44, 22.20% from 45 to 64, and 15.90% who were 65 years of age or older. The median age was 37 years. For every 100 females there were 95.70 males. For every 100 females age 18 and over, there were 94.20 males.

The median income for a household in the county was $34,406, and the median income for a family was $43,636. Males had a median income of $31,703 versus $21,341 for females. The per capita income for the county was $17,509. About 9.20% of families and 12.90% of the population were below the poverty line, including 17.00% of those under age 18 and 11.20% of those age 65 or over.

Cities and towns
Incorporated cities
Name and population (2005 estimate):

Winfield, 11,861 (county seat)
Arkansas City, 11,581
Udall, 766
Burden, 553
Dexter, 350
Atlanta, 250
Geuda Springs, 205, of which only a small portion lies in the county, the majority of the area and population being in Sumner County
Cambridge, 101

Unincorporated places
Akron
Floral
Grand Summit
Hackney
Kellogg
Maple City
New Salem
Otto
Rock
Silverdale
Tisdale
Wilmot