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The trail era – 1931 and after
The Michigan Road was the second great road to cross Olive Township, not the first. Northeast of the townsite, through the ground where Samuel Garwood sold his prairie tract to Jonathan Hubbard about 1836 and Hubbard laid out the town of Terre Coupee — the place that took its working name from Hamilton's hotel — ran the older road: the Sauk Trail, the Indigenous path from the Detroit country to Chicago, worn single-file across the prairies and remembered in the literature as one of the continent's great trails. The National Register nomination for the Haven Hubbard Home at 31895 Chicago Trail — the federal record for the Hamilton ground, read first-hand — states its course in one sentence: the village stood "on the Chicago Trail, also known as the Sauk Trail, an important stage coach route from Detroit to Chicago." Two stage roads thus crossed one township in the 1830s: the old trail northeast–southwest through Hamilton, and the new state road east–west through the Bourissa ground; and for a generation the trail's town was the greater — "At that time Hamilton was the great business center for this part of St. Joseph county," Chapman writes — until, in Chapman's own verdict, "the railroad has been built through the county and made a station at New Carlisle, [and] Hamilton has run down." The railroad chose between the two roads, and it chose the Michigan Road's town. The trail's road kept its name into the automobile age and took a number's errand besides: in May 1931 Michigan's highway commissioner announced the Chicago Road southwest of Niles rerouted by Bertrand and Chicago Roads into Indiana "to a connection with US-20 near New Carlisle," a southwesterly extension of the Niles trunkline — the old trail still feeding traffic to this town's highway a century after the stages. Chicago Trail remains the road's name on the ground today, carrying the county addresses of the Hamilton settlement — the Haven Hubbard Home among them — three miles northeast of the town it once outshone.
Principal sources: National Register nomination, Haven Hubbard Home (reference 13000091), read first-hand; Chapman (1880), the Terre Coupee and Hamilton account; Elmore Barce, "The Old Chicago Trail, and the Old Chicago Road," Indiana Magazine of History XV (1919); the Michigan trunkline record of May 1931 (michiganhighways.org, Historic US-112 listing).