Each April, Leesburg hosts Bikefest — three days of motorcycle culture that draws over 300,000 riders from across the southeastern United States and beyond, filling the downtown streets with bikes, music, and vendors. The scale is genuinely impressive: live bands on multiple stages, bike shows and custom competitions, stunt exhibitions, tattoo contests, food courts, and demo rides.
If motorcycles are your thing, this is one of the best rallies in Florida. If they are not, April is probably the wrong time to visit — the town is overwhelmed and accommodation books up months in advance. The festival typically runs the last weekend of April; check the city's website for the exact dates each year.