Like so many Northern Michigan communities, Cheboygan began as a Native American settlement. It wasn't until 1844 that the first white men arrived. It was later the county seat in 1853. There was a theater built in town in 1877.
Around 1890, ferryboats started using Cheboygan as a home port for traveling to the nearby Bois Blanc Island in the Straits of Mackinac. These ferryboat services are still around even today.
In 1914 and 1915, Cheboygan was home to the Flagler Cyclecar Company, a brass era cyclecar maker.
The former U.S. Coast Guard cutter and icebreaker Mackinaw claimed Cheboygan as it's home port from 1944 to 2006. In 2006 a replacement cutter by the same name of "Mackinaw" took it's place.
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