Trail Running calendar near Chesapeake 2026-2027

Cross country at Bells Mill Park with a 5 km race, a 1.5 mile kids course, and a competitive 5 km walk. Early registrants get guaranteed T-shirts and all finishers receive medals; awards across multiple age groups.

A mostly trail, low frills half marathon at York River State Park on June 7 2026 with a new Hike a Half option, marked trails, aid stations, and a five hour time limit.

Experience summer trail running on the dirt paths of Sandy Bottom Nature Park. This three race series offers increasing distances from 5k to 5 miles to support local scholarship funds.

Night Owl 9k at Freedom Park in Williamsburg VA is a night trail race over single track, fire road and paved trails with rolling hills and technical sections. Post race activities include pizza, beer and wildlife education.

A two mile timed dune run and a one mile Color Fun Run take place at Jockey's Ridge State Park on July 3, 2026. Proceeds support Friends of Jockey's Ridge and the event includes awards and a post race gathering.

Trail-based multi-hour event at Windsor Castle Park in Smithfield, VA with 10 hour, 5 hour, 2 hour and one-lap 5k options on a 3.1 mile loop that gains about 150 ft per circuit.

A women only 5K obstacle mud run with 18+ obstacles at Historic Greenbrier Farms in Chesapeake, VA on July 19, 2026. Open to participants aged 7 and up, the event welcomes running, jogging or walking and emphasizes teamwork and fun.

Muddy Dash Richmond on July 25, 2026 is a mud run 5K at Virginia Motorsports Park featuring obstacles, waist deep mud pits, and pre party and after party entertainment with music and food. Family friendly options include value and VIP packa..

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake, VA on a 1.5 mile loop with lake views and forested sections. The unpaved, tree-lined course has one aid station and is limited to 60 runners.

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.

A five-loop 25K at Jockey's Ridge State Park on October 10, 2026 where runners complete one 5K each hour for five hours; individual and two-person team entries are chip timed with awards by total time.

A Halloween themed 4 mile trail run and hike at York River State Park on a new course that includes dirt trails, rolling hills, single track and riverside views. The format is non competitive with finisher medals and post race refreshments.

Greensprings 24 is a 24 hour loop endurance race in Williamsburg, VA on October 24, 2026. The USATF certified course, multiple distance awards, team tracking, and proceeds benefiting The Arc make it a timed endurance event.

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.

Virginia Beast 2026 is a multi day ruck and endurance event in Virginia Beach based out of LFT Gym on 6 to 8 November 2026. Multiple distances are offered and competitors must carry ruck loads of 40, 50, and 80 pounds.

A 50K race on the Noland Trail at Mariners' Museum Park in Newport News on November 7, 2026, offered as a solo 50K or as relay teams of two to six, with festival access included.

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..

Timed trail events at Windsor Castle Park in Smithfield, VA, on a marked 5 km loop, offering 10K, 4 hour and 8 hour run and ruck options. Laps are counted, a stocked aid station serves hot items, and all finishers receive a homemade medal.

A trail event at Pocahontas State Park on December 12, 2026 offering 5K, 10K and half marathon distances through the wooded Bright Hope Trail area. Walkers are welcome and virtual entry options are available with medal and shirt choices.

Experience a two loop trail ultramarathon through the scenic First Landing State Park in Virginia Beach. Enjoy a supported 50 km course followed by a post race celebration with pizza and refreshments.