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Lakeside, like its Harbor Country sister towns, is a vacation destination and a popular choice for weddings at the historic Lakeside Inn. An active homeowners’ association sponsors several events during the year and fosters a strong sense of community. Many of the area's leading interior design firms are located in Lakeside. An active homeowners’ association sponsors several events during the year and fosters a strong sense of community.
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 other towns developing at the time, one of the first orders of business was to establish a sawmill. But it wasn't until the 1850's and the arrival of the Wilkinson family when real progress began. The Wilkinson's bought 2500 acres of land along the lakeshore.
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 post. Wilkinson was renamed Lakeside in 1874 for reasons that remain unclear. At about that time most of the woodlands along the lake had been cleared and residents began a gripe that continues today. John Wilkinson complained that he couldn't afford the taxes on his land. The taxes were $6.00 [Yes... Six Dollars].
The early visitors were often administrators and faculty members from the University of Chicago. In the 1920's the Chikaming Country Club was established. A replica of Shakespeare's birthplace was dismantled in Chicago and transported to Lakeside where it became the Chikaming 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 by Wilkinson heirs, Nadra and Al Kissman. Wilkinson Village 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.
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