The Sternwheel Regatta was an-end-of-the-summer festival held in Charleston from 1971 to 2009. In 1971, 13-year-old Nelson Jones, son of a prominent river family, approached Mayor John Hutchinson to suggest a race between five sternwheelers on Labor Day on the Kanawha River. Prodded by his secretary, Henrietta Cook, Hutchinson embraced the concept. Cook, herself a devoted river person, remained a major force behind the festival for many years.

Within two years, the boat races had expanded to a two-day festival centered around Charleston's downtown levee. It continued to evolve as organizers added music, fireworks, food vendors, a distance run, and numerous land-based activities. By the early 1980s, the Regatta had stretched to a week. It subsequently burgeoned to 10 days, attracting thousands of local people as well as river lovers from other states. In 1989, more than 50 boats converged on Charleston.

But the event wasn't without problems. Over the years, there was controversy over beer sales, a source of considerable revenue. Some felt crowds had become too raucous and beer sales were restricted. In 2000, festivities were scaled back to an extended weekend. Sternwheelers docked along barges moored in the Kanawha, dwarfed that year by a special guest, the grand Delta Queen. The legendary riverboat had made several appearances at the annual festival. Participation by sternwheelers was less in following years, and the races were discontinued in 2003. Difficulty in obtaining sponsors for expensive activities and performers led the city to discontinue the Regatta entirely in 2009. Over the years other attractions, such as FestivALL, had begun to attract larger crowds, and the city decided to place more emphasis on these newer events. After a 13 year hiatus, the Sternwheel Regatta returned for the July 4 weekend in 2022 and 2023.