Lakeside Harbor Country Located by Beautiful Lake Michigan Warren Dunes State Park Pictured

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The Story of Lakeside

Soon after Wessel Whittaker founded New Buffalo, newly arriving pioneers must have thought the village was a bit congested.  Perhaps they simply wanted less expensive land.  Whatever the reason, the area's expansion moved north across the Galien River to what is now Lakeside.  An original settler named the new community "Chikaming", an Indian word meaning "at the shore of the sea".

As with the other towns developing at the time, on eof the first orders of business was to establish a saw mill.  But it wasn't until the 1850s and the arrival of the Wilkinson family when real progress began.  The Wilkinson's bought 2500 acres of land along the lake shore.  They focused their energies on the area that is now the intersection of Lakeshore Road and Pier Street.  A trading post, boarding house and assorted other enterprises were established.  But the jewel of the village, naturally called Wilkinson, was a 600-foot pier.  The Wilkinson family's schooner, the Enterprise, took lumber and bricks to Chicago and returned with supplies for the now thriving trading post.  Wilkinson was renamed Lakeside in 1874.

In the late 1800s, with a train now stopping in the community, Lakeside's tourist industry began to flourish.  The early visitors were often administrators and faculty members from the University of Chicago.  In the 1920s the Chikaming Country Club was established.  A replica of Shakespeare's birthplace was dismantled in Chicago and transported to Lakeside where it became the Country Club's Shakespeare House.

As Lakeside was developing, and the current Red Arrow Highway was constructed, the original Wilkinson Trading Post was moved from its lake location to its current home on Red Arrow where it was eventually restored as Wilkinson Village and now houses an interesting museum which traces the history of Lakeside.

The Lakeside Inn is probably the village's most historically romantic site.  Movie stars were wined and dined there.  And during Prohibition, the tale goes, Al Capone along with a variety of Chicago politicians used the Inn as a favorite drinking and gambling spot.

Historical information courtesy of the Harbor Country Chamber of Commerce.

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