[1] This area was first settled in 1844 by Vermont natives Alfred and Mary Ames, who purchased property that included the present site of the Lakeside Inn.

A small settlement was established nearby in 1846; when the Chicago and Michigan Lake Shore Railroad was constructed in the late 1870s, a station was built at the site, then called Lakeside.

[2] In 1901, John J. and Nancy E. Aylsworth purchased several tracts of land at Lakeside, including the property on which this inn now stands.

Wilson converted the inn into the "Lakeside Center for the Arts," running his print business in part of the downstairs and taking in artists from across the country.

[3] The Lakeside Inn is a 2-1/2 story, broad fronted, side gabled wood frame structure sited on a low rise overlooking Lake Michigan.

A pair of cross gables face the lake, as does an open shed-roof veranda which extends across the entire facade.