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For centuries, bands of natives traveled it in single file, on missions of peace or war, until they had beaten a narrow pathway deep in the soil. The natives, traveling overland, picked the shortest safest route for easy trotting, often following paths worn by deer or buffalo. Being partial to low ridges but went around hills, lakes, swamps and places thick with thorny underbrush, that is why the Sauk Trail is so crooked.
When the white men came they followed it - LaSalle and other explorers, fur traders, missionaries, and parties of soldiers. The early settlers traveled it on horseback.
The trail became a major road in the 1760's by the British and the Colonists. In the early 1800's it became a military road connecting Detroit, once known as Fort Pontchartrain to Fort Dearborn (Chicago).
Surveyed in 1825 and built in 1829-36. Chicago Road had many sections that were paved with huge logs covered with dirt. Even before the road was improved, land hungry settlers traveled west from Detroit via the Chicago Raod. Now called Michigan Avenue, also US Route 12. Route 12 is also now a Scenic Byway.
Around 1838 the Potawatomi in Michigan., Indiana and Illinois sadly traveled it to the Mississippi and their new homes farther west.
Like the Cumberland, Santa Fe and Oregon trails, the Great Sauk Trail
made history. Four flags have been carried over it: French, Spanish,
English and American. The Indians had no flags.
Today this section, now US 12, is still paved with cobblestones.