The first STP took place in 1979 and was a race. From 1979 - 2019, the ride took place every year including 1980 when the route was changed because of the eruption of Mount St. Helens, also ending in Seattle. In 2020 and 2021, the event was cancelled due to the COVID-19 pandemic. From 1981, the Cascade Bicycle Club changed the event from a race to "recreational ride". Jerry Baker from Seattle was the winner of the first STP race. Baker, and Paul Wantzelius from Maple Valley, Washington, were the only riders who attended every consecutive STP, until their deaths, Wantzelius in 2010 and Baker in 2015. Despite being a cycling event people have taken part on unicycles, inline skates and two skateboarders have done it using a technique known as long distance skateboard pumping.