Connecting Washington Park and Gage Park is the once-majestic Garfield Boulevard. Although Garfield might lack the grandeur of its youth, this boulevard is home to some of the most fascinating historic sites on the South Side of Chicago.

Located at 319 East Garfield Boulevard is the original Garfield “L” station house. Built in 1892 as part of the expansion project designed to provide direct access to the World’s Columbian Exposition, the Garfield station house is the oldest station facility on the "L.” Although the CTA demolished the platforms during the construction of a new, modern, steel and glass Garfield station, the original station house was designated a Chicago Landmark on December 12, 2001.

Toward the end of the 19th Century, Garfield Boulevard became a prime location for successful Chicagoans to build lavish mansions and estate homes. Located at 736 West Garfield Boulevard is the 33-room mansion built for “Big Jim” O’Leary, the son of Catherine O’Leary, whose cow was once believed to have (the cow has since been absolved) knocked over the lantern that started the Great Chicago Fire. Just south of Garfield Boulevard is the Raber House. An unknown architect built the home as the centerpiece of the 6-acre estate of businessman and politician John Raber in 1870. Only slightly further south of Garfield Boulevard on 63rd Street is the Englewood Post Office. Although the site looks innocuous today, it was once home to Englewood’s most notorious resident and America’s first serial killer, H.H. Holmes. Holmes designed his hotel at this location to attract young women visiting Chicago for the 1893 World’s Columbian Exposition. The hotel was a maze of secret rooms and vaults, and even housed a crematorium. When he was apprehended, Holmes confessed to the murder of 27 women, although the actual body count could be higher.

Also located on Garfield Boulevard is the former Schulze Baking Company Plant. Built in 1914, the factory was once the home of the Butternut Bread Company. Although the factory is now abandoned, the building was listed on the National Register of Historic Places on November 12, 1982.