The original town company was composed of Orville C. Brown, President; S. C. Pomeroy and Mr. Ward, of New York. The town site was surveyed in February, 1855, by A. D. Searl. The name Osawatomie was formed by combining Osa, of Osage, with "watomie" of Pottawatomie, the creek by the latter name uniting just below with the Marais des Cygnes, and forming the Osage River (according to early chroniclers).

The first building on the town site was erected by Samuel Geer. it was used by him for a dwelling and boarding house. The first blacksmith was Mr. Holdridge, in 1855, and the same year Dr. Darr opened a drug store. the first child born was a daughter of Mr. and Mrs. Charles Foster, in December, 1854. The first marriage was that of Andrew Doler, to Miss Hughes, in the fall of 1854, and the first natural death that of a child of John R. Everett, early in 1855. During the same year John Serpell, who lived near Osawatomie, was accidentally drowned in the Marais des Cygnes while bathing.

The first lawyer in the town was C. H. Crane. Samuel Geer opened the first store in 1855, and also kept the first hotel which was burned at the sacking of Osawatomie in 1856. He was also the first Postmaster, being appointed December 21, 1855, when the postoffice was first established. In 1858 he built a two story frame hotel 40 x 50 feet, costing $3,000. It was in this hotel that Horace Greeley made a speech to an assembly of about 5,000 people in the spring of 1859, at the organization of the republican party in Kansas.

The first school house was taught in the winter of 1857-58 by Mr. Squires, in a frame schoolhouse. The present schoolhouse is composed of two parts, one stone, the other frame; total coast, $4,000.

The first church organized was the Congregational, in April, 1856, by Rev. S. L. Adair. Until 1861 the society held services in private houses and the schoolhouse, when they built their present stone church edifice at a cost of $2,150. Membership at the time of organization, 7; present membership, 18. Mr. Adair has, with the exception of three years, been pastor of this church since its organization.

The Methodist Church was organized in 1856. Their present frame church building was erected in 1881, at a cost of 41,500.

The Emigrant Aid Company, which selected the location for the town, sent out a saw-mill in 1855, and Barker to one set it up and manage it. It was a circular mill, propelled by steam and of great use to the early settlers. It was located on the south bank of the Marais des Cygnes, about a half mile below the town site.

The "First Battle of Osawatomie" occurred June 7, 1856, when John W. Whitfield, with about 170 Missourians, plundered it. At this time there was no killing of the inhabitants nor burning of their dwellings. The town was almost entirely defenseless, of which fact Whitfield had been informed by a young man, a stranger, who had for a week previously been boarding at Mr. Geer's and who acted a as guide to Whitfield's forces. Several dwellings and stores were plundered, and horses carried off. The village, at this time, consisted of about thirty buildings, actual population about 200.

The "Second Battle of Osawatomie" occurred August 30, 1856, a full account of which is given in the general history of the county. Notwithstanding these battles and the general troubles of the times, Osawatomie grew and prospered, and in 1857 was a town of considerable importance, having a population of about 800, 200 of whom were voters. Since this time it has made but little progress, has rather declined. At the present time it contains two general stores, two groceries, two hardware, one drug, and one furniture store, one lumber yard, two hotels, three blacksmith shops, one wagon shop, two churches and about 600 inhabitants.

The Insane Asylum
This institution was established for the benefit of the insane of Kansas. It is located about one mile northeast of Osawatomie, on high ground overlooking the surrounding country. By an act of the Legislature, approved March 2, 12863, William Chesnut, of Miami County; I. Hiner, of Anderson, and James Hanway, of Franklin, were appointed commissioners to locate the Asylum, and instructed to locate it in Osawatomie Township, on a tract of not less than 160 acres of land, affording practicable building stone, water and other facilities for the erection of suitable buildings, title to the land to be secured in fee simple to the state by donation.

By an act approved February 1, 1865, a board of three trustees was to appointed by the Governor, each to hold office six years, one of whom was to be appointed every two years. Under this act, Hon. James Hanway, Rev. S. L. Adair and A. Gove, were appointed the first Board of Trustees. Under the law approved March 6, 1873, the number of trustees was changed to six, each holding office for three years, two being appointed each year. By an act approved March 4, 1876, and which took effect March 10, the asylums for the blind, for the deaf and dumb, and for the insane were all placed in control of one board of five trustees, called the state Board of Charitable Institutions. the first board under this law consisted of Thomas T. Taylor, W. B. Slosson, John T. Lanter, John H. Smith and Joseph P. Bauserman.

The resident officers of the asylum, consist of a superintendent, steward and matron. The superintendents, with the commencement of their terms of service, have been as follows: Drs. C. O. Gause, May, 1866; W. W. Updegraff, May, 1869; C. O. Gause, November, 1869; C. P. Lee, November, 1871; L. W. Jacobs, November, 1872; A. H. Knapp, November, 1873; S. B. West, spring of 1877; A. P. Tenney, November, 1877; A. H. Knapp, present incumbent, November, 1978.

The institution owns 160 acres of land and numerous buildings. The main building consists of the central part and two wings, erected at different times since 1866, and completed in 1881, at a total cost of $350,000. In addition there are a dwelling house, ice house, barn and cow stable.

Previously to 1874, each county supported its own insane asylum, but during the Legislature session of that year an act was passed by which the Insane Asylum was placed upon the same basis as to support with the other State Institutions and has since been supported by appropriations from the state Treasury.

The Soldiers' Monument
The Osawatomie Monumental Association was organized August 6, 1872, the trustees being H. B. Smith, H. H. Williams, and Rev. S. L. Adair. The Charter of the association is dated November 4, 1872. the object was "to erect a monument to the martyrs who fell in the battle of Osawatomie, August 30, 1856." The bodies of these martyrs were removed from their original resting places, and re-interred in 1860, in a private cemetery in the west part of the town, donated for that special purpose by Charles A. Foster.

The monument which stands immediately over the graves of the martyrs, was prepared and erected by the Hallway Bros. of Lane. It was dedicated August 30, 1877, the twenty-first anniversary of the battle. Just previous to its erection, a suggestion was made to the association, that it would be appropriate to also place an inscription on it in commemoration of John Brown, Sr. who commanded the battle. This suggestion was acted upon, and accordingly the monument bears the following inscriptions:

Placing this inscription upon the monument has caused the original and primary object of the association to be obscured. It gave color and tone to the dedicatory orations and exercises, quite different from what they would otherwise have been, and caused the monument itself to be called "John Brown's Monument" which it was not designed to be and is not, but is the Monument of the Martyrs who fell at the battle of Osawatomie, August 30, 1856.

The Dedication of the Monument- The monument erected to commemorate the martyrs to liberty who were killed at the battle of Osawatomie, August 30, 1856, was dedicated August 30, 1877. Ex-Gov Charles Robinson, presided, made a brief address, and introduced the orator of the day, Hon. John J. Ingalls. After the eloquent oration of Senator Ingalls had been delivered, addresses were made by Hon. Dudley C. Haskell, Judge James Hanway, Col. D. R. Anthony, John Ritchie, Ex-Gov. Charles Robinson and others.

The citizens of Osawatomie, on the day of the dedication, contributed money to build the white picket fence around the cemetery, and provided dinner for a large number of those present. The number in attendance was about 10,000.

The following extract from the Okolona States, published at Okolona, Miss., was published soon after the dedication of the monument:

Societies and the Press
Osage Valley Lodge, No. 24, A. F. & A. M was originally organized in October, 1858, with nine charter members, The officers were as follows:-Squires, W. M.; Robert Lapsley, S. W.; Sylvester Underhill, J. W.; Fr. H. S. Greenough, Sec.,; Dr. S. C. Parish, Treas.; L. C. Crittenden, S. D.; L. D. Williams; V. I. Willis and John Sofield.

Osawatomie Lodge, Knights of Honor, No. 2725 was organized in 1882, with eighteen members. The officers were as follows; Reuben Smith, dictator; S. R. Mudge, past dictator; A. F. Meek, financial reporter; William Chestnut, reporter; J. C. Chestnut, treasurer.

Osawatomie Chapter of the Order of the Eastern Star, No. 26 was organized in January, 1882, with eighteen members and the following officers: Mrs. F. A. Maynard, W. M.; Henry Parker, W. P.; Mrs. Carrie Chestnut, A. M.; A. F. Meek, Sec.; J. C. Chestnut, Treas. the chapter now has twenty-six members.

Thomas Taylor & Brother own a combined saw and grist mill on the Marais des Cygnes, near the mouth of the Pottawatomie. It is propelled by steam during the periods of low water. The saw mill was erected in 1864; the grist mill was added at a later date.

The Southern Kansas Herald was established near the beginning of the year 1857, by Charles E. Griffith. In December, 1858, J. M. Kane bought an interest in the paper, which he retained about a year, selling out to Griffith. July 1, 1860, B. F. Kinter, who had purchased the paper, removed it to Paola, after which it was purchased by Col. G. A. Colton, who changed its name to the Argus and sold it to McReynolds & Kane. In May, 1866, McReynolds sold his interest to Colton. In August the paper was purchased by W. H. Johnson, who removed it to Iola, and it was discontinued in the fall.

The Osawatomie Times was established in 1881, by W. C. Paul. Its publication was continued only one year.

The Battle of Osawatamie
by William G. Cutler (1883)
This was the most memorable battle of the Border War. It was fought August 30, 1856. Capt. John Brown, Dr. W. W. Updegraff and Capt. Cline commanded the defense, and Gen. John W. Reid the attacking party of 400 Missourians. Gen. Reid's command, after crossing the Marias des Cygnes, at Bundy's Ford, four miles northwest of Osawatomie, approached the town about daylight, Rev. Martin White acting as guide. Frederick Brown was making preparations to return to Lawrence that day, and on his way to Rev. S. L. Adair's, met Gen. Reid and Rev. White with a small body of men in advance of the main force. He saluted them with "Good morning, boys; are you going to Lawrence to-day?" Rev. White replied:"Why, I know you!" and taking deliberate aim with his rifle, fired at Brown, shooting him dead in the road, about a mile west of town. This was twenty minutes before sunrise. Messengers were immediately dispatched to notify the people in town, and Capt. Brown, who was a half-mile east of town.

He, Dr. Updegraff and Capt. Cline collected their men together as rapidly as possible. At first it was designed to make use of the block-house as a defense, but learning that Reid had a cannon with him, this plan was abandoned and Brown and his men, forty-one in number, all told, took up their positions in the timber along the south side of the Marais des Cygnes, facing south; Capt. Brown, with seventeen men, on the right, Dr. W. W. Updegraff with ten men, in the center, and Capt. Cline, with fourteen men, on the left. There was also an independent command still further to the left, in the Emigrant Aid Company's mill, consisting of "Pap" Austin, an ex-regular soldier, and his large rifle, to which he had applied the fancy name of "Kill Devil", carrying an ounce ball.

When the forces were arranged in the woods the enemy was passing within about 600 yards of them, Mr. Holmes, a volunteer, advanced towards the top of the hill, on the southwest of the town to reconnoiter, and finding the enemy close at hand, fired at them, striking one of them in the mouth or chin and causing him "to bleed like a pig" as one of his companions afterwards expressed it. He then retreated to the woods, the enemy following him closely and forming a line from O. C. Brown's house to William Chestnut's premises-the high ground west of where the "John Brown monument"now stands. They then fired three guns, as they afterwards stated to Robert Reynolds, one of the prisoners whom they took, as a signal to the State force to surrender.

Capt. Brown had given orders to his men not to fire a shot until he gave the orders, but when these alleged signal guns were heard, the men became so impatient, believing the enemy had opened fire upon them, that they could not be restrained. Jason Brown raised his gun to fire, and the rest under Capt. Brown's immediate command did the same, although as one of the number states,"they knew it was contrary to orders." This first attack, which was made on the right wing of the Free-state line, was partially repulse, when the enemy brought up their cannon and placed it in position within about 400 yards of the timber where Capt. Brown's men were stationed, at each successive shot moving it farther east to scour the timber.

The cannon was loaded with grape shot but did no damage, the missiles passing over the heads of the men. During this time the Free-state forces kept moving east and returning the fire of the enemy, who finally ceased firing the cannon, dismounted and made a charge in to the timber when the main body of the Free-state men, having gallantly held their ground for an hour against ten times their number, were compelled to surrender or retreat. Most of them escaped across the Marais des Cygnes, some swimming and others in a skiff. Robert Reynolds, H. K. Thomas and Charley Keiser were taken prisoners by Capt. Warren Harris, of Platte county, MO and taken under guard to the town.

While attempting to swim his horse across the river, George Partridge was shot. Samuel Wright sprang into the river on the same horse, swam across, and, by means of the bushes climbed the steep bank on the north side of the river and escaped. The Missourians, on entering the town, commenced to pillage and burn it, first firing on the block-house, in which were stationed several men, who escaped before the cannon was brought up. There were no women in town except those belonging to the families of Messrs. Chestnut and Sears. Every house but four was burned-Mr. Starkey's, Mr. Woodbury's and two small cabins. The invaders left town with twelve covered wagons, two filled with wounded men and a large part of the remainder of the plunder.

As General Reid's command approached the town in the morning, David R. Garrison and George Cutter, who remained in the house of Mr. Carr over night, attempted to escape to the timber along the Pottawatomie, and give the alarm to the town. A detail of Missourians was made to pursue them, Garrison was killed, and Cutter seriously wounded and left for dead. The invading force retired from the town about 10 o'clock a. m., taking with them as prisoners William Bainbridge Fuller, Robert Reynolds, Charley Keiser, H. K. Thomas, Mr. Morey, young Spencer Brown, who was taken prisoner at the burning of his father's house, and William Williams, from Miami Village.

Of these prisoners, Williams, formerly of Westport, Mo., which place he had been forced to leave on account of his free-state proclivities, was taken to the edge of the town site and there shot; Charley Kaiser was shot September 1-the second day following. Keiser was one of the party under Captain John Brown who captured F. N. Coleman, the murderer of Charles W. Dow, at the battle of Black Jack, and Coleman had then made threats against him. When therefore, Keiser found that Coleman was among his captors, he declared to his companions his belief that he would be killed.

The party encamped, Sunday night, on the east side of Cedar Creek, on the old Sante Fe road, and Keiser was taken out on Monday morning to a guard of Kickapoo rangers and shot. Besides the Free state losses mentioned, must be added Theron P. Powers, who was, at the time of the invasion, lying sick in a house near the timber. He crawled out of the house and into the woods for protection, and was lying there completely exhausted, when he was found by the ruffians and shot.

Among those who participated in the defense of Osawatomie were John Brown, Sr., Captain; Dr. W. W. Updegraff, Captain; --Cline, Captain; Harrison Updegraff, Charley Keiser, Cyrus Tator, George Ferris, August Bondi, Robert Eaton, George Grant, George Partridge, William Partridge, Samuel Wright, J. M. Anthony, William Quick, Hugh Kilbourn, William A. Sears, ____Mills, R. W. Wood, D. W. Collis, Capt. Holmes, H. K. Thomas, James Clark, J. J. Holbrook, Jacob Benjamin, Caleb Shearer, __Baker, __Woodbury, Henry Kilbourn, Freeman Austin, Luke Parsons.

As before stated, Frederick Brown and David Garrison were killed on the approach to the town, and George Cutter badly wounded; George Partridge and T. P. Powers were killed during the progress of the battle and the retreat; William Williams on the outskirts of the town and Charley Keiser at Cedar Creek. Dr. Updegraff and D. W. Collis were wounded. The Freeman Austin, or "Pap Austin," alluded to, was encountered on the return march of the Missourians. After burning and sacking the town, they started eastward, with the purpose of crossing the Marais des Cygnes, in the vicinity of the Emigrant Aid Company's mill. Here they encountered Austin and the "kill devil" Austin opened fire upon them, calling out "Come on boys, plenty of men here," loading and firing as rapidly as possible. Not anxious to encounter "plenty of men" Reid faced about and left Osawatomie by the way he came, crossing the Maria des Cygnes at Bundy's Ford, four miles above.

The Free-state men who escaped re-assembled at a log house north of the river, Brown and Updegraff among them. The next day they removed to the south side, and commenced fortifying another camp, but were prevented by sickness from carrying out their design.

The losses of the Missourians are not generally known--probably not much greater than those of the Free-state men. There are numerous surmises and guesses as to what those losses were; but according to Reid's own statement, it was two killed and a few wounded. The disparagement in number-ten to one - and with but eighteen of the number armed with Sharpe's rifles, was too great for Capt. Brown or any of his men to reasonably expect to win a victory, even if they had had plenty of ammunition. The most that could be done under the circumstance was to make a show of resistance, and to retreat across the Marais des Cygnes when their ammunition was exhausted, which they did.

Nothing was ever done by the Free-state forces to punish Gen. Reid for thus attacking and destroying a defenseless town, or to interrupt his return march to Missouri, except a faint feint by Gen. Lane, at which he was adept.

Geography
Osawatomie is located at 38°30'6N, 94°57'3W (38.501650, -94.950799) along the Marais des Cygnes River. According to the United States Census Bureau, the city has a total area of 11.6 km² (4.5 mi²). 11.5 km² (4.4 mi²) of it is land and 0.1 km² (0.1 mi²) of it (1.11%) is water.

Demographics
As of the census of 2000, there were 4,645 people, 1,781 households, and 1,130 families residing in the city. The population density was 403.9/km² (1,045.0/mi²). There were 1,947 housing units at an average density of 169.3/km² (438.0/mi²). The racial makeup of the city was 92.21% White, 4.16% African American, 0.47% Native American, 0.22% Asian, 0.04% Pacific Islander, 0.75% from other races, and 2.15% from two or more races. Hispanic or Latino of any race were 2.54% of the population.

There were 1,781 households out of which 34.7% had children under the age of 18 living with them, 44.9% were married couples living together, 13.3% had a female householder with no husband present, and 36.5% were non-families. 31.6% of all households were made up of individuals and 14.1% had someone living alone who was 65 years of age or older. The average household size was 2.42 and the average family size was 3.03.

In the city the population was spread out with 27.2% under the age of 18, 9.9% from 18 to 24, 30.0% from 25 to 44, 18.6% from 45 to 64, and 14.3% who were 65 years of age or older. The median age was 34 years. For every 100 females there were 90.6 males. For every 100 females age 18 and over, there were 91.9 males.

The median income for a household in the city was $29,104, and the median income for a family was $37,172. Males had a median income of $30,650 versus $23,043 for females. The per capita income for the city was $15,353. About 10.9% of families and 12.9% of the population were below the poverty line, including 16.5% of those under age 18 and 10.6% of those age 65 or over.