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.
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
Trail races of 3 and 7 miles at Pilot Mountain State Park finishing at the summit, limited to 150 runners, with shirts, awards, and post-race breakfast.
January 2027
Trail races at Salem Lake on January 8 and 9, 2027 offering a night 5K, looped 12.5K to 50K distances, and a four person 50K relay.
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
A winter 5K at Jamison Park with in-person and virtual options, finisher medals for all and awards by overall, masters, and age groups.
April 2027
Trail races at Bur-Mil Park in Greensboro on April 24, 2027 offering a half marathon and a 4 mile course plus ruck, hike, and virtual options with shirt and medal.
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.
September 2027
A muddy obstacle run offering a 5K or Fun Run where participants tackle obstacles that test strength, agility and stamina while proceeds support YMCA health programs.
October 2027
Halloween themed 5K at Divine Llama Vineyards in East Bend, NC with a vineyard visit featuring llamas, chip timing by J3 Timing, wine pour, and a $35 entry fee.
May 2030
Conquer mountain trails in the scenic Uwharrie Mountains of North Carolina. This chip timed fundraiser offers 5K and 10K distances featuring forest paths, mountain summits, and beautiful lake views to support local youth camp scholarships.