Trail Running calendar near Chesapeake 2026-2027

A women only 5K obstacle mud run at Historic Greenbrier Farms on July 19, 2026, featuring 18 plus obstacles and welcoming females aged 7 and up who prefer a non competitive, team oriented outdoor event.

Muddy Dash Richmond on July 25, 2026 at Virginia Motorsports Park is a non-competitive 5K with obstacles, mud pits, and on-site Pre-Party and After-Party festivities. Family-friendly registration options include value and VIP packages.

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake VA on repeated 1.5 mile loops. The tree lined, unpaved course circles the lake, has one aid station, and is limited to 60 runners.

Join the community at Newport News Park for a 5k run across grass, gravel, and paved trails. This accessible local event offers a varied multi surface course through the scenic park grounds.

A trail 5K along the historic Roanoke Canal and a Half Mile Fun Walk in Roanoke Rapids, with proceeds helping replace historic batteau replicas and age-group awards for finishers.

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.

Experience the scenic beauty of Pocahontas State Park at this trail festival featuring a loop course 10k and half marathon. Enjoy runnable trails and professional timing in a picturesque Virginia forest setting.

Test your endurance at Jockey High Ridge State Park by completing a 5k loop every hour for five hours. Run the full 25k solo or pair up with a teammate to tackle this unique coastal loop challenge.

First annual 4 miles trail run and hike at York River State Park on October 10, 2026. Dirt trails include single track and gravel, the format is non competitive, all finishers receive medals and leashed dogs are allowed.

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 certified 2.215-mile loops, with distance awards, on-site support, team tracking, and proceeds benefiting The Arc in Williamsburg.

A trail half marathon at First Landing State Park with sandy sections, roots, bridges, and about 300 feet of elevation gain; includes event shirt, finisher beanie, donuts, and age-group awards.

The Low Key Halloween Haunts will take place in Charles City on Sunday 25 October 2026. You can run between 3 and 6 miles.

Virginia Beast 2026 is a multi-day rucking event in Virginia Beach on 6 to 8 November 2026. Events vary in distance and competitors must be prepared to carry 40 lb, 50 lb, or 80 lb rucks.

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.

A free Thanksgiving community event at Pocahontas State Park featuring a cross-country 5K and a short kids fun run. Registration is required; the day includes alumni photos, raffle drawings, and optional donations for a memorial award suppo..

A multi-format running and rucking event at Windsor Castle Park in Smithfield VA with a marked 5 km loop, a 10K option, timed 8 and 4 hour formats, lap counting, rucking divisions, and finisher medals.

A 24 hour ultrarun on the Roanoke Canal Trail using an out and back *10k* loop with start and finish at Weldon Mills Distillery on the Roanoke River. Held December 5 to 6, 2026; registration opens August 1, fee $120.

Multiple USATF certified races take place on the Dismal Swamp course in Chesapeake, VA, including 50K, marathon, half marathon and a 50K relay. Aid stations are provided and finishers receive apparel and medals.

Trail races at Pocahontas State Park include 5K, 10K and a half marathon on the wooded Bright Hope Trail, with virtual options available; walkers are welcome.