History

Tradition, tourism, and much, much more.

Okauchee was settled in 1839 by Orson Reed who built a mill at the current Foolery’s location. His mill was the first building constructed in the community and provided lumber for the nearby Watertown Plank Road in 1850. The following year the McConnell’s constructed a stagecoach inn to serve travelers along the Plank Road. This building still stands at the east end of the roundabout–at the center of downtown Okauchee. Within two years, the village also had a railroad depot at the end of Shady Lane, before the current highway 16 was constructed.

It was in the early part of the twentieth century that Okauchee became a resort destination for Milwaukeeans and people from the Chicago area. Tourists came by train and walked or were picked up to go down Shady Lane to The Landing on Okauchee Lake. The Landing was orginally a meeting place but eventually became a building and place of business for lake visitors. This building still exists today and is a family residence. From The Landing, stairs were taken down to the lake shore to board boats that escorted them to the many resort hotels and cottages on the lake. By 1927 Okauchee boasted eleven hotels among its complement of tourist-oriented businesses.

During the years of prohibition, many of these hotels were run by gangsters operating bootlegging enterprises, brothels, casinos and speak easys.

Okauchee and Okauchee Lake continues to be home to many full-time and seasonal residents and is still a very popular destination for outdoor recreational activities as well as dining and entertainment.

Before becoming a hotel/saloon/ice cream parlor, the Old Mill was a saw mill that used water power. It was a major supplier of wood planks for the construction of Watertown Plank Road.
A destination for nightlife in the early 1900’s. The island had a dance hall, bar, restaurant, private party rooms and hotel rooms. It is reported that Chicago gangsters would hang out and hide here at Wandt’s Island Park.
Tourists arriving to Okauchee by train would walk down Shady Lane to the public landing area where there were boats waiting to take them to their lake destinations.
Okauchee’s first train depot was in place in 1855. The depot was an essential means by which tourists and lake residents could easily reach the lake and locations thereon. It was located at the end of Shady Lane before Highway 16 was built.

For more historical information about Okauchee and surrounding lake country areas, visit these sites: oconomowochistoricalsociety.org or waukeshacountymuseum.org Or on these pages on Facebook: Epic Tales of Okauchee Lake, Okauchee Lake, Okauchee History & Memories, or Okauchee School.