The annual Webster County Woodchopping Festival celebrates the area's timbering heritage. Each Memorial Day weekend, lumbermen from the United States and other countries participate in woodchopping and sawing events. The Webster County festival is one of three world championship woodchopping competitions.

Webster County native Arden Cogar Sr., who began competing in woodchopping events in 1956 and won championship titles in the United States and Australia, organized the first Webster County Woodchopping Festival in 1960. Held in various places in the county in its early years, the festival was moved to its permanent location at Bakers Island Recreation Area in Webster Springs in 1965.

Cogar was the all-around champion of the Webster County Woodchopping Festival six times from 1973 to 1980. Another champion is Melvin Lentz, also of Webster County, who achieved the honor in 1982, 1985, 1988, and yearly from 1990 to 1994. His son, Jason, is now a champion wood chopper. New Zealander Jason Wynyard won the championship in 2002 and 2003, and in 2004 and 2005 it was taken by residents of New York state. Arden Cogar Jr. won the title in 2007, and Jason Wynyard won again in 2010.

The festival has grown to include a week's worth of events, including arts and crafts, concerts, parades, car shows, a lumberjack breakfast, a 5K Run, and fireworks, but it is the Memorial Day weekend lumberjack contests that remain the highlight. Competition categories include the Jack and Jill cross cut, two-man cross cut, hot saw, solo chain saw, standing block, handicap chop, springboard chop, championship chop, and all-around champion. The festival now serves as the Southeastern U.S. World Championship for wood chopping, as some 100 timber sport athletes compete for total prize money worth more than $30,000.