The Green Bay Trail
Eleven or twelve thousand years ago, it is likely that woolly mammoths traveled along an Ice Age migration path that formed the original Green Bay Trail. Geologist Herman Bender of the University of Wisconsin states that geologic and climatic conditions favored the woolly on its northward migration along the wikipedia:Moraine:Lake Border Moraine (an accumulation of earth and stones deposited by a glacier). Ice Age hunters followed in pursuit; evidence of this exists in Kenosha where spear points and woolly mammoth bones were discovered in the only confirmed woolly mammoth slaughter site east of the Mississippi River.
For many millennia after that, the history of the Green Bay Trail remains unclear, although indigenous tribes probably followed the path hunting and trading. In the 1600s French explorers Louis Jolliet and Father Jacques Marquette used the route in their travels, and it is also likely that French Canadian fur traders and coureurs de bois (“wood-rangers”) traversed the ancient trail. We know that tribes of the Algonquin family, most recently the Pottawatomie, used it until the early 19th century.
During the first decades of the 1800s, early settlers, remote from the more heavily traveled east-west transportation routes, welcomed the first mail carriers. Their nearly 500-mile round trip between Fort Dearborn in Chicago and Fort Howard in Green Bay took one month on foot in winter. (In summer the mail was sent by boat on Lake Michigan.) Pay for this extremely difficult trip was $60 to $70. Death by freezing and starvation, or at the hands of hostile tribes, was a frequent hazard. In 1832 an Act of Congress established the Green Bay Trail as an official post road, although it was marshy and nearly impassable for a horse and wagon. Locally the road, marked by trail trees, had what was known as a “wet” and “dry” route. The wet route ran along Ridge Avenue, Church Street, and Maple Avenue, which are on higher ground west of the ravines. The dry route ran closer to the lake near the present-day Sheridan Road.
The first stagecoach service began in 1836, with an open lumber wagon offering space for mail and passengers. Wooden roads were erected over rivers and ditches to aid passage. That same year, the Patterson Tavern was built near the Lloyd House on Sheridan Road. This and other wayside inns (including the log house "Bachelor Hall" built by Alexander McDaniel in 1837) were called “groceries” and sold liquor by the drink. Sometimes intoxicated patrons froze to death traveling from tavern to tavern.
In 1838 Congress appropriated funds for the construction of a road from the Illinois state line north to Green Bay, a convenient highway built along the west shore of Lake Michigan.