Winston-Salem
Trail Running Calendar near Winston-Salem 2026-2027
Explore the top trail runs near Winston-Salem for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A vineyard 5k at Divine Llama Vineyards on October 4, 2026 with chip timing, finisher medal, a wine pour, and age group awards on a grassy two lap course.
Trail races around three Greensboro lakes offering half, marathon, 40 mile and relay options, with virtual and ruck divisions and supported aid stations.
November 2026
A timed 5K run/walk at Starmount High School supporting Compassion Care Center, plus a 100 m Pastor Dash and awards across multiple age groups.
December 2026
A December trail event at Pilot Mountain State Park in Pinnacle, NC offering 3 mile and 7 mile routes that both finish at the summit.
An unstructured day of running in downtown Winston Salem where participants set their own distance and use a central aid station from sunrise to sunset.
January 2027
A weekend of trail races at Salem Lake offering a night 5K, looped 12.5K courses up to a 50K, and a four-person 50K relay, with water stops on looped courses, a seven hour cap for the 50K, finishers swag, and post-race food and beer.
A charity running event at Kimberley Park with multiple distances including a 49 mile individual option and a team relay, supporting HOPE of Winston Salem.
February 2027
An out-and-back 5K at Jamison Park in Winston Salem on February 14, with finisher medals for all and a virtual 5K option.
June 2027
Mud focused obstacle course in Pinnacle, NC with multiple 5K individual and team waves plus a 1200 m kids Pollywog race; fees vary by event.
A single-evening event combining four track races and a 5K cross-country race, with finishers receiving a t-shirt and car decal.
May 2030