This street, which runs a mere 200 feet from 4th Avenue to Yesler Way in front of City Hall Park, is named for George W. Dilling, who was mayor of Seattle from 1911 to 1912.

In 1911, Mayor Dilling took an empty lot that until two years earlier had been the location of the Katzenjammer Castle, Seattle’s second city hall, and converted it into what is now known as City Hall Park — originally named Dilling Park in his honor. In 1916, the municipal offices moved once again, to the newly constructed King County Courthouse, then known as the City–County Building, across the Jefferson Street right-of-way from the park. They remained there until 1962, but the park retains the “City Hall” name.

In a letter dated March 29, 1937 from A.C. Van Soelen, corporation counsel for the city, to the Board of Public Works, regarding the ability of the city to restrict parking on Dilling Way, he writes that “Dilling Way apparently never was established or named by ordinance or other action of the City Council and was opened up or paved in 1915 or 1916, presumably in lieu of Jefferson Street which was closed between Third and Fourth Avenue though never formally vacated,” and suggests that the city council “affirmatively declare its policy” regarding the street by passing an ordinance. Such an ordinance was passed shortly thereafter, making the name of Dilling Way official. (Interestingly, that ordinance refers to the street as a “private way,” but the county’s quarter section map shows it as a public road. That same map shows that the walkway in front of the courthouse is still, technically, Jefferson Street.)

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