Roscoe's Chili Challenge 2026
November 5–7, 2026 · Lakeland, Florida
About this event
Founded in 1986 and run on private ground north of Lakeland, this is one of the older traditional biker rallies still going in Florida, and it has not softened with age. The chili cook-off is real — cooking starts at eight on the Saturday morning and judging is at noon. Around it run mini-bike races, outhouse drag races, motorcycle shows, field events, arm wrestling, cornhole and a full weekend of live music, with an on-site FM station broadcasting the whole thing. The rules tell you exactly what kind of weekend it is: twenty-one and over with ID, no colours, no firearms, photographs fine but video prohibited, and tent campers must arrive on a motorcycle. Entry covers bike parking and tent camping; neighbouring landowners rent space for cars and RVs. Profits go to a child safety organisation. Finding it takes attention — the directions run off a landmark set of radio towers rather than a street address.
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