Trail Running calendar near Chesapeake 2026-2027

A 24 hour run and walk at Sandy Bottom Nature Park in Hampton VA on April 25 to April 26, 2026. Open to individuals and teams of two to twelve with registration opening January 1 and a field limit of 225.

A trail event at First Landing State Park in Virginia Beach featuring **60K** and **30K** routes across nine trails, coastal shoreline, and three aid stations; 60K is two loops, 30K one loop, both with a 10 hour limit.

Celebrate the 40th anniversary of this historic charity race through the Nags Head Woods Ecological Preserve. Run a 5K on gravel roads or enjoy a 1 mile walk to support local community initiatives in the Outer Banks.

Experience cross country racing at Bells Mill Park with 5K and 1.5 mile events featuring grass and marshy terrain. Enjoy a post race afterparty with catered lunch boxes and finisher medals for all participants.

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.

Conquer the iconic sand dunes at Jockey's Ridge State Park in this unique 2-mile run/walk. Your effort supports the preservation of the park. All finishers earn a medal and can celebrate at the post-race party.

A 10 hour loop event at Windsor Castle Park in Smithfield VA on a 3.1 mile trail with about 150 ft gain per loop. Event options include 10 hour, 5 hour, 2 hour and a one lap 5k and rucking is allowed.

Muddy Princess Virginia Beach is a women only 5k obstacle mud run at Historic Greenbrier Farms. Join a community focused on empowerment and fun while supporting the fight against breast cancer.

Experience a fun mud run at Virginia Motorsports Park featuring a dozen obstacles and waist deep mud pits. This untimed event focuses on enjoyment over competition and welcomes participants of all backgrounds to join the post race party.

A 12 hour endurance run at Oak Grove Lake Park made up of repeated 1.5 mile unpaved loops. The tree lined, flat course includes lake and forest scenery and is limited to 60 runners with no waitlist.

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.

A 24 hour endurance race at Greensprings in Williamsburg on October 24, 2026. Runners complete certified 2.215 mile loops on a mainly flat crushed gravel trail while supporting The Arc in Williamsburg.

A trail half marathon at First Landing State Park with roots, bridges, sandy sections and about 300 feet of elevation gain. The event includes four aid stations, shirts and finisher beanies, and supports AIDNOW.

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 endurance events at Windsor Castle Park in Smithfield, VA offer a 5 km loop with 10K, 4 hour and 8 hour run and ruck options. Laps are chip timed and all finishers receive homemade medals.