Winston-Salem Cycling Classic – Gears & Guitars

Spend Memorial Day Weekend in the heart of downtown Winston-Salem’s Innovation Quarter, where the excitement of high-speed cycling meets the energy of live music. At Bailey Park, grab a spot to watch top cyclists race past while enjoying a lineup of free concerts from big-name bands.

Indulge in bites from food trucks, sip drinks from nearby bars, and explore restaurants just steps away. Whether you’re cheering on the racers, soaking up the music, or unwinding with great food and drinks, Gears & Guitars delivers an unforgettable festival atmosphere—all in the middle of the action.

This year has tons of options for the whole family!  Two road distances (69 and 42 miles) and two greenway/gravel distances (15 and 7 miles). And everybody meets back at Bailey Park for lunch and a cold beverage afterwards.  

69-Mile Fondo – 8:00 AM

42-Mile Fondo – 8:30 AM

Greenway Ride – 10:00 AM

Join us all day for FREE live music at Bailey Park

Ears to the Ground – Noon

High School Reunion – 2:00 pm

Gods of Grunge – 5:00 pm

Saint Motel – 9:00 pm