Olean had its origin in the historic need for a convenient route to the Ohio country and the West. It was founded in 1804, when Ohio had just been admitted to the Union, and the West was the symbol of challenge and adventure to hundreds of pioneers eager to build a new nation.
The natural advantages of a navigation headquarters at the headwaters of the Allegheny River were readily apparent to at least one early surveyor, Major Adam Hoops.
Hoops, a Revolutionary army officer and a man of considerable political influence, had covered much of western New York, then known as the Genesee Country, as a surveyor for Robert Morris. Morris had vast land holdings acquired in the post-Revolutionary period when government policy encouraged speculation by selling new lands for a few cents an acre to pay its staggering war debts. Millions of acres were purchased, but by 1800 bankruptcy had overtaken many speculators and the lands were being divided into smaller blocks and surveyed for sale to enterprising pioneers. Morris, best known as the "financier of the Revolution", was one of those whose private speculation led to bankruptcy, and his western New York holdings were acquired by the Holland Land Company, from whom Maj or Hoops got 20,000 acres in 1803, including the site at the headwaters of the Allegheny. As a special favor, because of his close acquaintance with Alexander Hamilton and others of political prominence, Hoops obtained a deed to the tract, instead of the usual contract, for little more than his signature.
The site which Major Hoops envisioned as a navigation headquarters for the westward migration was a point of land formed by the junction of a creek with the Allegheny. In a letter dated April 15, 1804, Hoops wrote to Joseph Ellicott (surveyor for the Holland Land Co.) giving him instructions regarding the survey of his land and said, "It is proposed to me at New York to drop the Indian name Ischue or Ischua…(and) I have concluded to do as proposed. The neighborhood of Oil Spring (source of the first petroleum discovery in North America) suggests a name, different in sound tho’ perhaps not of different meaning, which I wish to adopt. It is Olean. You will do me a favor by assisting me to establish this name…
"…To begin, you will greatly oblige me by addressing the first letter you may have occasion to write me, after I receive the surveys to the Mouth of Olean". The name that was ‘different in sound tho’ not in meaning’ was derived from the Latin word oleum, meaning oil.
A map of the Village, prepared in 1808 by E. Johnson for Hoops, showed a public square, a site for a school, a ‘burying ground’ and several streets. Hoops planned a patriotic memorial in the village square (now Lincoln Park). The central thoroughfares were named Union and State Streets; other streets were named for Revolutionary generals who were his friends. Some of these streets retain their original names: Barry, Putnam, Wayne, Henley, Laurens and Sullivan.
As the great westward migration gathered momentum many hundreds of pioneers arrived each spring at Olean Point to await the flood tide to float their rafts and flat-bottomed boats, which they called arks, down the Allegheny to the Ohio. At the peak of the river traffic, around 1818, as many as 3,000 pioneers embarked during the season, and Olean Point was better known than Pittsburgh or Buffalo.
It was lumber more than navigation advantages that fostered the growth of a permanent settlement. The area was covered with magnificent stands of white pine, oak, hickory, beech, maple and ash. The Allegheny was a busy avenue of commerce. Huge rafts were constructed of large logs, strung together in barge lines and piloted down the river, usually by Indians. When they reached Pittsburgh, Cincinnati or New Orleans the rafts were taken apart and those logs sold also.
The decline of Olean Point as a navigation headquarters for pioneers going West began around 1825 when the completion of the Erie canal opened a direct route to the Great Lakes and the Northwest. By the mid-1830’s the lumber boom was also tapering off though rafting continued until 1851, when the Erie railroad was completed. For a while there was hope that the Genesee Valley Canal, a branch of the Erie Canal which extended from Rochester to the Allegheny River would revive the lagging commerce. But this project, which was begun in 1836 and completed in 1856, was never profitable and was abandoned in 1878.
Olean was incorporated as a village and granted its first charter by the legislature in 1854. The development of Olean as a city began when the Buffalo and Washington Railroad (the Pennsylvania) was finished in 1872. By 1874 Olean had become the railroad center of petroleum operations in the Bradford territory. The shipment of oil from Olean grew from a few barrels to more than 20,000 barrels a day. By 1878 there were 150 paying wells in the vicinity. Olean was incorporated as a city on April 25, 1893. By the early 1900’s Olean had become an established industrial center.