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Situated in northern Cheboygan County, for which it is the county seat, the City of Cheboygan, Michigan is at the mouth of the Cheboygan River on Lake Huron, in the northern Lower Peninsula.

The city and county were probably named for the Cheboygan River, which runs through the center of the city. The name is of Ojibwe origin, and settlement of the area was a continuation of the Ojibwe settlement, known as Shabwegan, which was there before the Native Americans were displaced by European-American settlers in the mid-1800s.

The chief routes through the city are US-23 and M-27. US-23 runs generally east-west through the center of the city, connecting with I-75 at Mackinaw City and the Mackinac Bridge, about fifteen miles to the northwest, and with Rogers City, about forty miles to the southeast. M-27 runs south from Cheboygan, along the north shore of Mullett Lake to I-75 at Indian River, less than twenty miles to the southwest. Lesser routes through the city include Black River Road, Butler Road, Levening Road, Old Mackinaw Road, and Riggsville Road.

Cheboygan's peak population was 6,859 in 1910. With the decline of the logging industry, the city experienced a couple of decades of sharp decline, which was not helped by the Great Depression. However, during World War II, a Naval Station was established on nearby Bois Blanc Island, and the US Coast Guard Cutter Mackinaw made Cheboygan its home part. This brought about a resurgence in the city's economy, which was further boosted by new industries. Although a slow decline began in 1960, the numbers have remained relatively stable, with a current population of just under five thousand.

Jacob Sammons, a cooper from Fort Mackinac, built a cabin on the site of an old Native American camping grounds in 1844, setting up a home and business in what is now the eastern part of Cheboygan. He recruited other craftspeople and settlers, and a community developed. In 1850, a post office was established there, called Duncan or Duncan City. Duncan was designated the county seat and the location of the federal land office in 1855.

Meanwhile, a separate town, named Cheboygan, was established west of Duncan in the 1870s, in the area where the railroad was expected to come through, although it wasn't until 1881 that the Michigan Central Railroad arrived. Later, the Detroit & Mackinac Railway established its northern terminal there, providing passenger and freight services. Passengers headed to Mackinac Island would disembark in Cheboygan, where they caught the ferry to the island.

Due to its rapidly growing population, the county seat shifted to Cheboygan in 1870, and Duncan was eventually absorbed into the expanded boundaries of Cheboygan.

Cheboygan was incorporated as a village in 1871 and became a city in 1889. Around that time, Cheboygan became the home port for ferries going to Bois Blanc, a nearby island in the Straits of Mackinac and, as mentioned earlier, it was the home port of the former US Coast Guard cutter and icebreaker Mackinaw, from 1944 to 2006, after which the port continued this role as the home port for its successor, also named Mackinaw.

Cheboygan Area Schools is a public school district offering a K-12 curriculum through East Elementary School, Cheboygan Intermediate School, Cheboygan Middle School, Cheboygan Area High School, Inverness Academy, and Cheboygan Virtual Academy.

The focal point of this guide is on the City of Cheboygan, Michigan. Websites representing the municipality or any businesses, industries, schools, places of worship, organizations, individuals, attractions, or events within the city are appropriate for this guide.

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