About Lakeside, MI
Lakeside is a small village in the heart of Harbor Country—just two miles from Union Pier and Harbert. It is also close to Harbor Country’s other popular resort towns: New Buffalo, Sawyer and Three Oaks.

Lakeside is home to several antique stores, boutiques, coffee shops and restaurants. In fact, that is about all there is in Lakeside. With a population just a little over 3,000, it is one of the smallest and quietest villages in all of Harbor Country.

The pristine Lake Michigan shoreline is the pride of Harbor Country. Anchored by two major public beaches—New Buffalo in the south and Warren Dunes State Park in the north—this stretch of unspoiled shoreline is an ideal spot to plan your Michigan vacation.

History
At the turn of the century, Lakeside was home to some of the most famous Lake Michigan lakeshore resorts; it was a popular vacation destination for nearby Chicagoans beginning in the early 1920s.

Lakeside's history began with logging that fed Chicago's need for lumber. Farming soon replaced the disappearing forests, and today, despite development, the land is lush and green.

Soon after Wessel Whittaker founded New Buffalo, Lakeside attracted newly arriving pioneers. One of the first settlers named the new community "Chikaming," an Indian word meaning "at the shore of the sea." In the 1850’s, the Wilkinson family bought 2,500 acres of land along the lakeshore.

The intersection of Lakeshore Road and Pier Street was one of the first areas to be developed—a trading post, boarding house and assorted other enterprises were established there.

But the jewel of the village 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.

When the woodland along the lake was cleared, residents began a gripe that continues today—that the taxes are too high. The taxes as the time were $6.00.

In the 1920's, the Chikaming Country Club was established; it was popular with administrators and faculty members from the University of Chicago. 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 Highway.

The Lakeside Inn is one of the village's first inns. Movie stars and a number of Chicago politicians used the inn as a favorite drinking and gambling spot. During Prohibition, Al Capone also spent time at the inn.