The city of Cortland, near the west border of the county, is surrounded by the town of Cortlandville.
Cortland, settled in 1791, was made a village in 1853 (rechartered in 1864), and was incorporated as a city in 1900 as the 41st city in New York state. When the county was formed in 1808, Cortland vied with other villages and won the status of becoming the county seat. Known as the "Crown City" because of its location on a plain formed by the convergence of seven valleys, Cortland is situated at above sea level. Forty stars representing the 40 cities incorporated before Cortland circle the State of New York and Crown on the city's official seal. The seven points of the crown create seven valleys depicting Cortland's seven surrounding valleys. The 41st star in the center of the crown illustrates Cortland as the closest incorporated city to the geographic center of New York.
The leading industry in Cortland in the late nineteenth and early twentieth century was the Wickwire Brothers wire drawing mill, noted for its production of wire hardware cloth for use as window screens. The extent of their wealth is commemorated in a pair of magnificent mansions. The Victorian Chateauesque style home of Chester Wickwire is now the 1890 House Museum & Center for Victorian Arts, while the 1912 home of Charles Wickwire is now owned and operated by the SUNY Cortland Alumni Association. It is open to the public as well as being used by the Alumni Association to host college-related events and house visiting dignitaries.
Cortland was also home to Brockway Motor Company, a pioneering truck maker. Begun in 1875 as Brockway Carriage Works, it was taken over by Mack Trucks in 1956, and survived until 1977. The city continues to host an annual show of Brockway trucks.
In 1868 Cortland became the home of the Cortland Normal School, now the State University of New York at Cortland.
In 2006, Cortland's historic clock tower burned down. It was later re-built, with spaces for both businesses and apartment style housing.