The block that would later become the site of the Pioneer Courthouse Square was first purchased in 1849 by shoemaker Elijah Hill for 24 dollars and a pair of boots. In 1856, the school board purchased the block, opening the first public school in Portland – Central School – in 1858. In 1883, Henry Villard bought the block as the site for a new hotel, and the school moved a block north to the present-day American Bank Building. The eight-story Portland Hotel, completed in 1890, contained 326 rooms, a restaurant, ballroom, billiard room, bar, ladies’ parlors, a telegraph office, and a news and cigar stand.
In 1951, Meier & Frank purchased the site; the hotel was torn down and replaced with a two-story parking structure. Much of the original stone foundation of the hotel remains under the sidewalks today. In the late 1960s, Meier & Frank proposed another parking structure, but this time plans included a much larger 11-story parking garage. The plan was denied by the City of Portland, prompting the development of a planning program for Portland’s downtown.
By 1974, Portland’s Downtown Plan included the development of a massive public space, the Pioneer Courthouse Square. The city purchased the block, and in early 1980, they announced an international design competition. Legend has it that the winner, a Portland-based team led by acclaimed designer Willard Martin, painted their proposed design on the parking lot that occupied the block before being chosen. The Pioneer Courthouse Square officially opened on April 6, 1984, with a massive celebration that had over 10,000 attendees. By 2004, Pioneer Courthouse Square reached 300 annually programmed event days.