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The development of Oswego took place primarily during the 19th Century. Smaller cities became centers where the agricultural population could find entertainment, cultural opportunities, books, newspapers, schools and involvement in government. Most of these smaller cities were centered around one area of development, such as mining centers of the west, or the coal mining areas of the east.

Oswego was unique among American cities because its rapid growth did not depend on just one circumstance or event. Shipbuilding was the first industry, beginning with the English occupation of the harbor in the early part of the 18th Century. The military history of the city began at the same time. The construction of the first fort, Fort Oswego in 1722, on the West side of the Oswego River was followed by Fort Ontario, constructed on the east side of the river in 1775.

The second major industry in the early settlement was fur trading, which developed into a major economic opportunity. It produced income for both France and England. With the conclusion of the American Revolution, development of the harbor and port of Oswego burgeoned. Salt, discovered on the shores of Onondaga Lake, was a product shipped via the Oswego River and ultimately over the Oswego Canal to all parts of the country. This led to expansion and development of the harbor as a major Lake Ontario port and soon it was a major spot for trains shipping grain from the western lakes.

Since the water was the principle means of power in the early days of the 19th Century, Oswego soon became a major milling center. By the mid-19th Century, the railroad had a presence and Oswego became known as the city where the water meets th rails. The city eventually became the home to what was to become the largest industry of its type in the United States. Kingsford Starch was developed here and became a major source of employment to hundreds of Oswegonians. Growing rapidly alongside Kingsford were the textile and boiler-making industries, which flourished for many years.

Gerrit Smith, a leader in the abolitionist movement, helped Oswego to become one of the most important stops on the Underground Railroad. He was a leader in other ways as well, and although not a resident of the community, built its first library and worked hard for the temperance movement, among others.

Edward Austin Sheldon founded the Oswego Normal School for teacher education, which today is Oswego State University. He developed what is known as the object method of teaching, which revolutionized American education. Oswego was also the home of Mary Walker, a Civil War surgeon and the only woman in the history of the United States to win the Congressional Medal of Honor.