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Unlike many other frontier towns, Sidney, Ohio, was not "carved out of the heart of a forest". The seventy acres were a thoroughly cleared and cultivated farm, said to have been first planted in corn in 1809 by William Stewart.

Shelby County’s Courthouse Square in downtown Sidney was selected as a Great American Public Place in 1995. In the early 1800s, however, there was a large swamp along what is now the east side of the square. In some places it was four or five feet deep and provided a "favorite swimming place for small boys".

According to the Memoirs of the Miami Valley, "We must picture a public square devoid of any form of comeliness previous to the building of the first brick courthouse in 1833. We must remember that it was surrounded for a great part of the year with rivers of deep mud, and that sidewalks were only a desultory public improvement — at private expense. It is quite possible that the first sheriffs’ pigs and chickens shared the public square with them."

"The growth of the town was rather slow. There does not appear at any time to have been a rush of settlers to the county seat, but rather a steady tide...that gradually filled the town. Building was generally of wood, but not of logs. Brick was not used for several years after the town began, but when it appeared it met with popular favor."

Under the 1787 laws of the old Northwest Territory was a provision for the act that required male citizens 16 years and older to work on the roads not more than 10 days a year, and stipulated a fine if they failed to carry out their assignments. In 1799, this condition was reduced to two days of public work and the age raised to twenty-one years.   The early roads in Shelby County will be found among those leading from Piqua to Wapak, from Troy to Dingmansburg (East Sidney), from Dingmansburg to Wapak, and from Piqua, or from the Piqua and Wapakoneta Road to Hardin and St. Marys.

During the 1870s ordinances were passed relating to the grading and care of streets, sidewalks and gutters. Due primarily to the actions of The Progressive Union, Sidney’s village improvement Society formed in 1892, there was much grading of streets/alleys in the mid 1890s and new streets opened or extended. An ordinance to ‘improve certain streets by paving them’ was passed June, 1903 (to be Main, Ohio, Court and Poplar).

Early photos show people, horses and other traffic moving through the muddy roads around the downtown square, while a 1910 booklet promoting Sidney lists among its civic improvements "paved and well-graveled streets." Over the years, streets have been constructed of a variety of materials, from the natural ‘dirt or mud’ road, to ‘corduroy’ [trees cut square and put down crossways], various mixtures of gravel, brick, cement and black-top.

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'Downtown' segment written in October, 1998 by Sherrie Casad-Lodge