Before 1700, this region was inhabited by Potawatomi peoples descended from Woodland Indians known as "mound builders".

[6] There are also reports that the Sauk Indian chief Black Hawk had a campsite on Oconomowoc Lake.

[6] The first white person recorded in the area was Amable (sometimes spelled "Aumable") Vicau, brother-in-law of Solomon Juneau, one of the founders of Milwaukee.

Blanchard acquired a claim adjacent to that of Sheldon on the other side of the lake, which he later sold off to Philo Brewer.

[6] The first recorded birth was that of Eliza Jane Dewey on January 19, 1840, in the lodgings above a chair factory located at 116 N.

[9] Initially buried at Zion Church point, she was eventually re-interred at Nashotah Mission.

[11] Such infrastructure encouraged further settlement, and by 1853 the town grew to a population of 250, with ten stores, three hotels, one gristmill, and one sawmill (both located near the present Lake Road bridge), and a schoolhouse.

[6] In August 1899 a professional golf tournament hosted by the Oconomowoc Country Club was won by Harry Turpie.

The church, which was built in 1913, was completely destroyed, except for the frame of its bell tower, which later had to be torn down as it was at risk of collapse.

The source of the explosion was an old gas line that had been capped off sometime in 1972–1973; it ruptured after having been struck by a backhoe as utility work was being done on Wisconsin Avenue in preparation for reconstruction of the street.

The original route passes through downtown Oconomowoc; however, a bypass was built which goes around Lac La Belle to the north.

[28] Amtrak's Empire Builder and Borealis passenger trains passes through Oconomowoc, but they do not stop.

Freight rail service is provided by Canadian Pacific Kansas City (CPKC).

Bus routes 904 and 905, operated by Waukesha Metro Transit, has its western terminus at the Collins & Cross Parking Lot station.

Originally called Henshall Place, it opened in 1851 on land that is now part of Fowler Park.

When the grounds became overcrowded, Charles Sheldon donated land for a new cemetery, and in 1864 the Wisconsin Legislature approved the transfer of burials from Walnut Street to the current La Belle Cemetery grounds on Grove Street.