Start with a guided interior tour of the Ernest Hemingway Birthplace. This beautifully preserved Victorian home, where the author was born and spent his first six years, showcases antiques and rare family photographs offering a glimpse at Hemingway’s early influences. You can also step into another time at the Nineteenth Century Club. Once the private women’s club for the area, this landmark structure now hosts public art, music, and cultural events.

Catch an afternoon performance in its stylish ballroom before checking out the Oak Park River Forest Museum. This new museum, housed in a restored historic firehouse, sheds light on these distinct communities with its rotating exhibits and never-before-seen artifacts. The Riverside Historical Museum, in Riverside’s historic downtown is another must-see for its compilation of archival material highlighting Frederick Law Olmsted’s landscape architecture. The village’s architectural legacy is also emphasized, from the famed village water tower to Frank Lloyd Wright’s Coonley House.