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Four flags have flown over this area: Spanish, French, English and American. This was part of the original Northwest Territory and was contained inside the borders of three states. Eight different Indian nations have lived on the Bay. Later settlers included European explorers, missionaries and fur traders. And more recently have been followed by the Yankees who platted and developed the lands, the railroaders, shippers, loggers, entrepreneurs and settlers.
All the people who came here seemed to have envisioned something special. They were optimists, opportunists, people of stubborn courage who braved harsh winters and primitive conditions to build a good life.
About the time Columbus arrived in the New World, the Chippewa people came to the land they called Sha-ga-waun-il-ong. This term has been translated numerous ways, it is either "lowlands", or the "needle". It may also be "the region of shallow water", where "there are large extended breakers". Each version is descriptive and suitably accurate.
The Chippewa stayed on Chequamegon Point for about a century before leaving it, first to settle on Madeline Island and then to move to the Sault region. In the years that followed, the Chippewa came and went to and from the Ashland area. Their travels were dictated by the necessities of hunting and gathering, by their long years of war with the Sioux and after 1659, the fur trade.
Two French fur traders, Pierre d'Esprit, le Sieur Radisson and Medard Chouart, le Sieur des Groseillers, were the first Europeans of record to visit Chequamegon Bay. They arrived in 1659 and built what has been called the first European dwelling place in Wisconsin. A historical marker is located at Maslowski Beach on US Highway 2 in Ashland. The monument was erected in 1929 by the Old Settlers Club.
The Chippewa heartily welcomed the Frenchmen. Five years later, Father Claude Allouez arrived. He was a Jesuit missionary and he brought the first word of Chirstianity to Wisconsin's shores. Allouez built a chapel not far from Radisson's and Groseillier's stockade and remained at the Bay until 1669.
In 1854, Asaph Whittlesey and another Ohioan named George Kilborn set out from LaPointe to explore the head of Chequamegon Bay. Whittlesey built a ten foot by fourteen foot cabin in Ashland. His wife Lucy and daughter Eugenia joined him in August and prepared to winter in their new home. Civilization quickly followed the Whittleseys to Ashland. The first community dance was held at their house. The Reverend L.H. Wheeler preached the first sermon on the first Independence Day that was observed there. It was the location of the first Post Office and polling place for county offices. Sunday school was also conducted on the premises.
Other dates of note:
- 1856 - The first plat of Ashland was registered
- 1870 - First Ashland brownstone quarried & shipped
- 1872 - First sawmill built by W.R. Sutherland
- 1877 - Wisconsin Central rail connects Ashland to Chicago
- 1877 - Chequamegon Hotel opens (one block from current hotel)
- 1887 - State legislature incorporate the City of Ashland
- 1889 - Wisconsin Central Depot constructed (recently renovated)
- 1892 - Northern Wisconsin Academy opens (Northland College)
- 1894 - Post Office built
- 1904 - Ashland High School opens
- 1929 - First airport opens
- 1940 - WATW radio goes on the air
- 1963 - Dedication of the Apostle Island National Lakeshore
- 1972 - Memorial Medical Center opens
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