Trail Running calendar near Chesapeake 2026-2027

A low key, mostly trail half marathon at York River State Park on June 7, 2026, run in a no frills Hike a Half format. The course includes single track, fire roads and about one mile of pavement, with aid stations and finisher medals.

A three-race summer trail series at Sandy Bottom Nature Park organized by the Peninsula Track Club, featuring 5K, 4-mile, and 5-mile events plus a full-series entry and awards across age groups and walker categories.

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.

A manually timed trail event at Windsor Castle Park in Smithfield, VA, run on a 3.1-mile loop with 10 hour, 5 hour, 2 hour and a one-lap 5k formats; aid station and rucking options are available.

A women only 5K obstacle mud run at Historic Greenbrier Farms in Chesapeake, VA on July 19, 2026. The course includes 18 plus obstacles and welcomes participants aged seven and up to run, jog or walk in a teamwork focused, non competitive s..

Family friendly 5K mud run at Virginia Motorsports Park in Richmond with obstacles, waist deep mud pits, a pre party and an after party with music and food. Standard and VIP registration options are available.

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake, VA, made of repeated laps of a 1.5 mile loop. The unpaved, tree lined course features lake and forest views 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.

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 Halloween themed 4 mile trail run and hike at York River State Park on October 10, 2026. The new trail features single track, river views and rolling hills, with finisher medals for all and a two hour time limit.

Hog Jog on October 10, 2026 in Smithfield, VA features an in-person 5K on Windsor Castle Park trails, a Piglet Kids Run with keepsakes, and a new Virtual 5K with result submissions throughout October.

A 24 hour loop endurance race in Williamsburg, VA on October 24, 2026. Runs use a certified 2.215 mile crushed gravel loop with distance awards and proceeds benefiting The Arc.

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 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.

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 and distance options on a marked 5-km loop at Windsor Castle Park in Smithfield, VA, including 8-hour, 4-hour, 10K and rucking categories; laps are counted and all finishers receive homemade medals.

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.

Races at Pocahontas State Park on December 12, 2026, offering in-person 5k, 10k and a half marathon through the wooded Bright Hope Trail. Walkers are welcome and virtual entry options are available.