The history of Cortland really began with the purchase of land in 1804 and 1805 in Bazetta Township by Edward Scoffield and John Budd who became the first permanent settlers. A short distance north of the Scoffield property, a little village of hand hewn log cabins known as Leroy began to emerge. Samuel Bacon purchased 40 acres of land along the Mahoning River in 1807. This land he traded in 1816 for a lumber mill owned by Bentley and Brooks, located on Water St., on the east side of Walnut Run. A small dam, built in 1809, provided water to run the mill only in the spring when the stream was high. When J.H. Post later purchased 80 1/2 acres, and H.G. Scovill 10 acres along Walnut Run, these two men built a much larger dam, the water covering 12 ½ acres. The water was used to run their custom and planning mill near the intersection of Water and Plank Streets. It was the only mill of its kind for miles around.
Across the street, the two also owned a grist mill operated by a large wooden water wheel which turned on a wooden shaft 25 feet below. Later, this mill was run with steam. Enos Bacon, a son of Samuel, opened a store and at once set about making improvements to suit the needs of local residents. He platted part of his property into lots and developed them, and thus was born the community which has evolved into the Cortland of today. The Bacon settlement became known as Baconsburg. After a railroad was laid in 1868, four trains traveled the route through the community, making frequent stops. The railroaders called it the Baconsburg Stop because of the many Bacon families who lived in the village.
With the railroad came more people, more money and more commerce. One who came was a traveling minister, Orrin Gates, who formerly had lived in Cortland, New York, in the Lehigh Valley. Gates settled in Baconsburg where he became the regular minister of the Disciple Church. The oldest church in Cortland, it had been founded by members of the Baptist faith in 1818, and became a Disciple Church in 1832. Baconsburg soon became a thriving town of 614 persons. There were three churches, two newspapers, stores, mills, industries and a variety of businesses. There were two livery stables, a smithy, and two hotels for the accommodation of traveling salesmen, railroad workers and coach travelers.
As one result of the growth brought about by the coming of the railroad, the village fathers set about the task of incorporation. After a four-year period, the petitioners accomplished their goal on May 7, 1873. Minister Gates, who by this time had acquired some influence in the community, managed to give the name of his former home in New York State to the newly incorporated village which now became officially known as Cortland. The incorporated portion contained a one square mile area, and so it remained until the 1950's when annexation produced the existing village limits.
Cortland became a well established community, and a village hall was erected in the fall of 1874. The building was remodeled in 1968, but was demolished after a new building was built on North High Street in 1986. The Methodist Episcopal Church (now the United Methodist Church) was organized in 1820. A cheese factory was built by David Everett in 1875, which had a capacity of ten boxes of cheese a day. The cheese boxes were furnished by Amos Larnard who had a cheese box factory on Plank St. These boxes were made from virgin lumber which was readily available in those days. Cortland had become known for its educational advantages, and now the early citizens made a special effort to secure a good location for a commodious Union School building. The main purpose of this new school was not only to furnish education for Cortland citizens, but also for those living elsewhere in Trumbull County and adjoining areas.
The lot was chosen and the school erected, ready for occupation in 1877. It was hailed as the mecca for all who had a desire to seek higher education, and it became noted for its high standards. A portion of this building still remains, although it has been remodeled at intervals to suit changing times. It is currently vacant. A Cortland Volunteer Fire Department was organized in 1885, and consisted of a bucket brigade. Later, a tanker with a manpowered pump was obtained. The water was drawn from the mill pond on Walnut Run. Later, cisterns were dug at strategic locations about the town. A water system, completed in 1939, provided fire hydrants, another big step for the betterment of Cortland.
The old fire station, built in 1885, was torn down and replaced with a modern structure in 1949. An addition was made in 1964 to provide space for the up-to-date equipment in use today. Another addition was built in 1986. On Easter Sunday in 1981, Cortland officially became a city because the 1980 census had enumerated 5,011 residents, eleven more than the required number for a city. Having anticipated this change, a Charter Commission had been elected in 1979 and at the 1980 general election voters approved a charter form of government which became effective January 1, 1981.