Biggest Party on Two Wheels

Experience the Winston Salem Cycling Classic & Gears and Guitars on May 23-24, 2025—a spectacular way to kick off summer! Join thousands of cyclists and spectators in downtown Winston-Salem’s Innovation Quarter for a festival that fuses world-class amateur and pro cycling events with electrifying live music from national and local acts. This unique weekend features fast-paced drag sprints, route options for all riding styles, and a Saturday packed with criterium racing and unforgettable concerts. Whether you’re a competitive racer, casual rider, or music fan, this is the city’s signature celebration on two wheels!

• Friday features the 4th Street Drag Sprints on a flat, urban road strip in downtown Winston-Salem.

• Saturday offers community Fondo rides with both road and gravel/greenway options (distances vary) and technical downtown criterium racing at Bailey Park.

• Free live concerts by major bands (e.g., Switchfoot) and local artists
• Exciting Friday night drag sprints with on-street dining and drinks
• Community fondo rides for all cycling levels
• Pro and amateur criterium races on Saturday
• Family-friendly festival atmosphere