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).

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.

Ashland is a city in Ashland and Bayfield counties in the U.S. state of Wisconsin. It is the county seat of Ashland County. The city is a port on Lake Superior, near the head of Chequamegon Bay. The population was 8,216 at the 2010 census, all of whom resided in the Ashland County portion of the city. The unpopulated Bayfield County portion is in the city's southwest, bordered by the easternmost part of the Town of Eileen. The junction of U.S. Route 2 and Wisconsin Highway 13 is located at this city. It is the home of Northland College, Wisconsin Indianhead Technical College, and the Sigurd Olson Environmental Institute.

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.