Williamsburg
Trail Running Calendar near Williamsburg 2026-2027
Explore the top trail runs near Williamsburg for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
AUSA Southern Virginia Chapter hosts a timed 3rd Annual 5K and 10K on the Virginia Capital Trail in Charles City, with race timing, a finisher medal, event SWAG, and proceeds supporting the Charles City High School JROTC Scholarship Fund.
October 2026
Hog Jog in Smithfield on October 10, 2026 features an in-person 5K through Windsor Castle Park, a Piglet Kids Run, and a Virtual 5K with medals and T shirt included.
A 24-hour loop endurance race in Williamsburg VA on a USATF certified 2.215 mile crushed gravel course with multiple distance awards and on-site amenities.
Halloween-themed 5k and 10k at Indian Fields Tavern/5 Fields Brewing Co. with costume judging, official timing, finisher medal and a finish-line beer.
November 2026
Experience the only race held on the scenic Noland Trail in Newport News. Runners can tackle the 50 km distance solo or as a relay team while enjoying a post race festival with live music and tastings.
Multi-format running and rucking event at Windsor Castle Park in Smithfield VA featuring a marked 5 km loop, timed 8 and 4 hour options and a 10K.
January 2027
Snowy Owl 10 Mile is a winter trail race at York River State Park on Jan 3, 2027, featuring technical single track, fire roads, and about 600 feet of elevation gain. The course includes three aid stations and a finisher medal.
Looped 5 km trail course at Sandy Bottom Nature Park in Hampton VA with 8 hour, 4 hour and 5 km options and cupless aid station support.
A half marathon and a 5K at Harwoods Mill Park in Yorktown on January 17, 2026, with shuttle parking from McReynolds Athletic Complex. Limited fields, four aid stations, on-site packet pick-up and specific trail conditions.
April 2027
24-hour solo and team run in Hampton, VA on April 24, 2027, held on a flat 3.75 mile dirt park loop with a limited field and a history of cancer fundraising.
June 2027
Windsor Castle 10 Hour is an endurance event in Smithfield VA on a 5 km loop with manual lap counting, team options and a rucking division.