For the Town of Ashland, see: Ashland (town), Wisconsin. Ashland is a city in Ashland and Bayfield counties in the U.S. state of Wisconsin. The city is a port on Lake Superior, near the head of Chequamegon Bay. The population was 8,695 at the 2010 census. The city is situated at the junction of U.S. Route 2 and Wisconsin Highway 13. It is the home of Northland College and the Sigurd Olson Environmental Institute.