The Western Cherokee Nation was organized in 1840, creating nine districts: 

1, Sequoyah; 

2, Illinois; 

3, Canadian; 

4, Flint; 

5, Goingsnake; 

6, Tahlequah; 

7, Delaware, 

8, Saline and 

9, Cooweeschoowee. 

Tahlequah was designated the national capital. Flint and Goingsnake Districts were combined to create Adair County, which was established at the Oklahoma Constitutional Convention in 1906. Originally designated as Indian Territory, Oklahoma became a state in 1907. The City of Stilwell and the Towns of Watts and Westville were established. 

The region is part of the Ozark Plateau foothills of the Boston Mountains, with the Illinois River running through it. 

Clement Vann Rogers, Will Rogers father, was born in January 1839, a month before the Cherokees arrived over the Trail of Tears to where the Baptist Mission is today. When Clement was three years old, his father Robert Rogers, was killed on July 1842, reportedly by ‘Ross men’ for signing the Removal Treaty of New Echota. He was buried on the family property. His grave is marked by the Oklahoma Historical Society. Other Will Rogers kin are buried there as well. The old homestead had belonged to Robert Rogers, with a tobacco factory, broom factory, general store, blacksmith shop and two slave quarters. William Musgrove was the next owner because he married Rogers’ widow Sallie Vann Rogers. Isaac Morris bought the homestead from Musgrove’s widow, Sally Vann Rogers, who was Will Rogers grandmother. 

Each district built a log courthouse, then in the 1880s the Cherokee Nation appropriated $1,200 for each district to build a wood frame court house. A courthouse was built in Flint, also called Town of Mays, on the banks of Sallisaw Creek, about a mile north of where Dahloneqah School is now.  Fairfield Mission was in 1829, Muddy Springs School opened in 1846, and a Post Office was established in 1846 with Walter Scott Adair named the first postmaster, and Flint Masonic Lodge was established in 1853. Adair was also a president of the National Temperance Union which was sponsored by the Fairfield Mission. 

The Civil War was fought from 1861-1865, dividing loyalties.

Families active in business in the Flint District are family names still recognized, as many relocated when the train came through what is now Stilwell: John Bell, John Sharp, Harrison Baden, W. N. Littlejohn, Baxter Choate, B.G. Fletcher, E.E. Starr, and George Taylor. Blacksmiths were Harrison Fletcher, B.G. Fletcher and Pole Hannah. Two cotton gins were operated by Ellis Starr and Pole Hanna. John Houseberg operated a hotel and later one in Stilwell.

In 1894 Cherokee Strip payments were made to Cherokee citizens at Flint Courthouse.

Adair County was named after an influential Cherokee family, William Penn Adair. Frank C. Adair was the first county sheriff. Frank Howard started the first bank, Guarantee Bank. Three doctors in the area were A. J. Sands, I.W. Rogers and Ezell W.G. White, who was also a Justice of the Peace. The Reverend Jesse Bushyhead, a Cherokee religious and political header helped bring opposing factions together to create the Cherokee Nation. He is buried here as is Going Snake.

January 2, 1897 in United States Court for the Northern District, I.T., in Muskogee, citizens J. P. Willis, William Allison, John Goss, J.H. Dannanberg, Flank Black and John Hunt, as agents of the Town of Stilwell,  I.T., filed for Incorporation. It was approved under W. M. Springer, Judge U.S. Court, Northern District, I.T. Rufus Allison was the first mayor. The first City Council elected in a special election were Ward 1- John A. Goodall and C. J. Carson; Ward 2 - Jeff Atkerson and R. L. Reese; Ward 3 - Paul B. Chambers and J.M. White; Ward 4 - James T. Worsham and C. L. Fletcher and Ward 5 - J.E. Chucuate and Jack C. Bone.

Marilyn Hill-Russell was the first female mayor and today Jean Ann Wright is mayor. Her father, Harold Moten, served on the council and as mayor.

In 1895 Stilwell appears on maps as a railroad division point.

Stilwell became the county seat about the same time the first governor, Charles Haskell was determined the winner after three elections in 1907. The community was founded with the construction of the Kansas City, Pittsburg and Gulf Railway, later named Kansas City Southern, which traveled from Missouri to Mexico. Arthur Stilwell brought his train tracks through Indian Territory, going around the Boston Mountains. 

Daniel Boone’s youngest son, Captain Nathan Boone, helped survey the land for a military road. Founded in 1838, Watt’s was name for John Watt’s, a Chickamunga Cherokee Chief. Westville was named for James West, a railroad attorney. A post office was opened in 1895.

A. J. Edmonton published the first newspaper in 1898, the Stilwell Times.

Numerous newspapers have reported local and national news in Stilwell, including the Stilwell Sentinel in 1901; the Stilwell Standard  from 1901 - 1910; in 1921 the Standard-Sentinel billed itself as the oldest newspaper in Adair County, with 585 issues that can be read at the Oklahoma Historical Society website. The Adair County Democrat, in April o6 1930, also claimed to be the oldest newspaper in Adair County, with Vol. 33 (33 years) and No. 12 (12 weeks since the beginning of the year). The Adair Gleaner 1916-1931.

The county consists of numerous communities, from the original 23, which are still active with churches, schools and community centers: Bell, Cherry Tree, Chewey, Christie, Elm Grove, Fairfield, Greasy, Lyons Switch, Marietta, Mulberry, Oak Grove, Old Green, Peavine, Piney, Proctor, Rocky Mountain, Salem, Titanic, Wauhillau, West Peavine and Zion.

In 1896 the first general store was established in Stilwell. 

In 1897 the population was of Stilwell was 779,  in 1900 it was 948 and in 1910 it was 1,039. In 1940 the Census reported 1,588 Stilwell residents. During post World War II the numbers were 1,949 in 1950 and 1,325 in 1960. In 1970 the Census reports 2,134 residents. In 1990 there were 2,663 residents and in 2000 there were 3,276. The 2010 Census showed an increase to 3,949 and 2020 Census reported 3,706 residents.

Agriculture has been a major part of the county, with wheat, sorghum, cotton, oats, corn, cattle and horses as principal products. Stilwell Canning Company was established in 1942. It became Stilwell Foods in 1974 and today the serves desserts (Mrs. Smith’s Pies) to the global market as Schwan’s. In the early 1930’s strawberries became a major crop with more than 2,000 acres grown and picked. In 1948 the Kiwanis Club hosted the first Strawberry Festival and in 1949 the State of Oklahoma designated Stilwell the Strawberry Capitol of the World.

Changes happened more quickly around the turn of the century. Citizen’s Bank and Trust open in Stilwell in 1901 and the Bank of Stilwell opened in 1902. The first telephones arrived in 1902. Statehood was 1907.

The first brick public school was built between 1908 and 1910.

A vote to establish an electric plant came in 1909 made it one of the first to have an electric plant. 

In 1910 Stilwell was officially declared the permanent County Seat.

In 1920 the first Adair County Courthouse was occupied and Amos Handle Factory opened making hickory handles. In 1929 the Courthouse burned. A new Courthouse was completed in 1931. The Bank of Commerce opened in 1931. In 1949 GRDA began providing electrical power to Stilwell and in 1952 Stilwell Foods offered frozen foods. In 1955 the new elementary and junior high were constructed. In 1956 the sheriff and sheriff-elect died in a shoot out at the court house.

In 1924 Dr. Thomas Williams opened a hospital.

In 1950 plans for a modern hospital, Stilwell Municipal Hospital, were under the leadership of Mayor Bruce Cox and druggist Jack Chaffin. Until then citizens here went to Tahlequah City Hospital or Elizabeth Hospital in Prairie Grove. In 1952 the 18-bed facility opened On the corner of Sixth and Oak. Carla Ann Keeter was the first baby born there. Today it is the Stilwell Elementary Cafeteria.

It was replaced by the $3.1 million Memorial Hospital which was financed without either city or county bond issues or tax assessments for the non-profit.

In 1982 the Cherokee Nation met medical and dental needs of Cherokee Nation citizens at a clinic in Stilwell or they went to W.W. Hastings Hospital in Tahlequah. In 1992 Chief Wilma Mankiller appropriated more than $7 million from the U.S. Congress to construct a new clinic, called the Wilma P. Mankiller Health Center, which was dedicated in 1995. In 2015 there was a $10 million expansion, and in 2022 the tribe added a $30 million expansion to the facility now with 110,000 square feet. In 2024 they began work on the Mary Holland Carson Health Center beside the Mankiller Clinic. The clinic and health center are on the north end of Davis Mountain, on land that was part of the Cherokee allotment of Mary Holland Carson’s family.

In 1946 the Stilwell City Charter was adopted. The Chamber of Commerce endorsed the effort to designate Stilwell as a city rather than a town, which meant greater autonomy and opportunity for growth. The Chamber of Commerce is also mentioned in 1946 in a newspaper story, that it was interested in working GRDA to supply power to the City. These are the first two references to the chamber.

The county is also known for infamous characters such as Belle Starr, Ned Christie, Frank and Jesse James and Pretty Boy Floyd.

Some who put Stilwell on the map are Larry Adair, former Speaker of the House of Representatives; the late Wilma Mankiller, Cherokee Nation first female Principal Chief; and football star with the University of Oklahoma and San Diego Chargers, the late Sam Chaphan. Not so publicly recognized was physicist John M. West, who worked on the atom bomb as part of the Manhattan Project.  

The 1960s brought more progress. 1963 street signs and house numbers were assigned for home mail delivery. Cherokee Nation Industries was established. 

In 1970 KCS Depot was deeded to the City. In 1971 the Community Building and swimming pool were built. In 1971 the Public Library opened. In 1978 Quantec, Inc. opened.

1980 brought the new high school, 1983 Mid First Bank opened and later becomes Armstrong Bank. In 1985 a runway was built at the airport. 

Tyson Foods, Inc. was opened in Stilwell in 1990. History of Adair County was published in 1992. And in 1997 the 100th Centennial Celebration was held.