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Trail Running Calendar near Yorktown 2026-2027

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Explore the top trail runs near Yorktown for 2026-2027! We've gathered 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Endurance races at Windsor Castle Park in Smithfield VA featuring a 5 km loop, 10K, timed 4 hour and 8 hour events plus rucking categories.
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.
8 hour and 4 hour training runs plus a 5 km event on flat loops at Sandy Bottom Nature Park in Hampton, VA.
A two-distance event at Harwoods Mill Park on January 17, 2026, featuring a half marathon and 5K with shuttled parking, marked trails, four aid stations, and participant limits.
April 2027
An 8k (5 miles) trail run or hike in Freedom Park, Williamsburg on April 4, 2027, with one aid station, health talks, preordered box lunches, and finisher medals.
May 2027
A fundraising event at Harbor Park featuring a stadium stair climb and a 2 mile run and walk along the Elizabeth River Trail.
June 2027
Ten-hour timed trail event at Windsor Castle Park in Smithfield VA with manual lap counting, multiple timed options, rucking choices and a cup-less aid station.
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