The unpopulated Bayfield County portion is in the city's southwest, bordered by the easternmost part of the Town of Eileen.

Four flags have flown over the area around Ashland from colonial to contemporary times: Spanish, French, English and American.

About the time Christopher Columbus arrived in the New World in the late 15th century, the Ojibwe people came to the land they called Sha-ga-waun-il-ong.

This term has been translated numerous ways: "lowlands", the "needle", "the region of shallow water", and where "there are large extended breakers".

Allouez built a chapel not far from the stockade erected by Radisson and Groseillier; he worked and lived at the Bay until 1669.

In 1854, Ohioans Asaph Whittlesey and George Kilborn set out from La Pointe to explore the head of Chequamegon Bay.

Local landowner Martin Beaser named the settlement Ashland after Kentucky statesman Henry Clay’s residence.

[6] In the nineteenth century, immigrants to the area included many individuals and families from Germany and northern Europe, as shown by the numerous Lutheran churches in town.

During the last year of World War I, from March–October 1918, six recorded incidents of vigilantism took place in the Ashland area, committed against men of German descent, who were suspected of pro-German sympathies.

A group identifying as the Knights of Liberty claimed responsibility for the attacks, saying in a letter to a local paper, "We have no purpose to do injustice to any man, but we do feel that any treasonable and seditious acts, or utterances, demand prompt punishment.

"[7] Victims included: Governor Emanuel Philipp expressed his indignation over these incidents, as well as reports of local ethnic Germans receiving threatening letters.

His investigator found the local citizenry uncooperative, including John C. Chapple, editor of the Ashland Daily Press and campaign manager for Roy P. Wilcox, a Republican candidate for governor proclaiming his own patriotism.

Haven threatened to send a company of the state guard to maintain law and order in the area.

Two months after the world war ended, newspapers reported that the local Knights of Liberty had disbanded.

[24][25] The harbor of Ashland was dominated by the massive Wisconsin Central Railway (later Soo Line) ore dock, built in 1916 to load iron ore mined in the area into freighters bound for industrial ports in the Midwest, such as Ashtabula, Ohio, where steel was produced.

[27] The main concrete structure and trestle had slowly deteriorated since the early 1970s because of lack of maintenance and the effects of the environment.

On May 14, 2009, the Ashland Planning Commission granted Canadian National Railway approval for demolition of the dock.

[32] Ashland has a humid continental climate (Koppen: Dfb) with four distinct seasons and notably cold winters.

In the United States House of Representatives, Ashland is part of Wisconsin's 7th congressional district.

A few of the largest manufacturers in the community include: Many small businesses also make up a large portion of the local economy.

Stations serving Ashland come from the Duluth market: The two major highways in the city are US 2 and WIS 13.

[40] However, after flooding in 2016 caused substantial damage to bridges south of town, CN discontinued service to Ashland (trains now reach only as far north as Park Falls).

Airports certified for commercial carrier operations near Ashland: Other public use airports near Ashland: Local transportation is provided by the non-profit Bay Area Rural Transit (BART) system, which has bus stops throughout the community.

Headquartered in Ashland's Industrial Park, BART also provides transportation to and from other communities in the Chequamegon Bay region, including Washburn, and Bayfield.

[42] Northern Towns Transport is a regional car service and shuttle provider, connecting Ashland and the Chequamegon Bay area with downtown Minneapolis, Minnesota and Minneapolis-St. Paul International Airport; as well as the Twin Ports of Superior, Wisconsin / Duluth, Minnesota and Duluth International Airport.

The Chequamegon Symphony Orchestra (CSO) provides orchestral concerts to the residents of northern Wisconsin.