Cook County is a county in the U.S. state of Minnesota. As of the 2020 United States Census, the population was 5,600, making it Minnesota's seventh-least populous county. Its county seat is Grand Marais. The Grand Portage Indian Reservation is in the county.

Ashland County is a county located in the U.S. state of Wisconsin. As of the 2010 census, the population was 16,020. Its county seat is Ashland. The county was formed on March 27, 1860, from La Pointe County.

Madeline Island is an island in Lake Superior. Now part of Ashland County, Wisconsin, it was long a spiritual center of the Lake Superior Chippewa. Although the largest of the Apostle Islands, it is not included in the Apostle Islands National Lakeshore. It is the only island in the Apostle Island chain open to commercial development and private ownership. The community of La Pointe, located on the western edge of the island and established by French colonists as a fur trading post, was one of the earliest European settlements in the area. It has a population of 302, with a higher population during the summer tourist season. The island can be accessed by ferry from nearby Bayfield.

Bayfield is a city in Bayfield County, Wisconsin, United States. The population was 487 at the 2010 census. This makes it the city with the smallest population in Wisconsin. In fact, for a new city to be incorporated today, state regulations require a population of at least 1,000 residents, so it would have to be incorporated as a village instead.Wisconsin Highway 13 serves as a main route in the community. It is a former county seat, lumbering town, and commercial fishing community, which today is a tourist and resort destination. There are many restaurants, hotels, bed & breakfast establishments, specialty shops, and marine services. This tourism industry is largely built around Bayfield's status as the "gateway to the Apostle Islands" (i.e., the primary passenger ferry port).