In the late 1400's the Chippewa Tribe moved into the Chequamegon Bay area. They lived there for over 100 years. The need for new hunting and gathering grounds and their constant battles with the Sioux caused them to move in and out of the Ashland area until the arrival of European explorers. In 1659, French explores Pierre d'Esprit and Medard Chouart arrived in Chequamegon Bay as the first recorded Europeans in the region. They lived peacefully alongside the Chippewa Tribe and started the area's fur trade.

Europeans stayed in the bay area and continued the fur trade until they had over hunted the animals whose pelt they relied on. In 1854, two settlers left LaPoint to explore Chequamegon Bay. Asaph Whittlesey and George Kilborn built cabins in what is now Ashland. Their families soon joined them along with others. Soon more and more settlers moved to Ashland and it became a thriving community. Ashland has continued to grow and now has a population of almost 9,000. The town is steeped in rich historic heritage, which is best illustrated by Ashland's Historic District.

The downtown is lined with historic buildings, shops and restaurants including the Soo Line Depot. Being placed right on the shores of Lake Superior, Ashland is full of recreational opportunities. Sunny summer days can be spent swimming, fishing or boating in the waters of Lake Superior. Not far from Ashland you'll find Copper Falls State Park. The park has canyons, streams and waterfalls for your viewing pleasure as you hike by. Every July Ashland celebrates Ashland Bay Days featuring an off-road bike race, 10K run, sailboat race and numerous arts and crafts displays. For fun by the lake Ashland is the place to be.