The Cascade Cycling Classic was the longest-running elite road bicycle racing stage race in the United States, held from 1980 until its final edition in 2019, with the 2018 event canceled and the 2020 race scrapped due to COVID-19. Based in Bend, Oregon, it was a regular fixture for North America's top cyclists and was managed by the Cascade Cycling Classic Youth Foundation, led by race director Bart Bowen, a former pro and two-time national champion who won the race himself in 1993. The men's roster of winners reads like a who's who of cycling, including Lance Armstrong (1998), Levi Leipheimer (2008), and Francisco Mancebo (2011–2012). The women's competition, which saw a brief pause between 1991 and 1998, was headlined by champions such as Kristin Armstrong (2005, 2008) and Evelyn Stevens (2009). Serving as a crucial proving ground for talent across the continent, the classic highlighted the best of both domestic and international competitors before its curtain call in 2019.