Trail Running calendar near Chesapeake 2026-2027

An out-and-back ultramarathon of more than 200 miles from Sandbridge Beach through the Outer Banks to Cape Hatteras Lighthouse. The event raises funds for veteran suicide prevention with all proceeds split between Awareness N Action and Mis..

A point to point ultra on the Outer Banks from Corolla to Hatteras with 100% paved coastal roads. Events include 100 mile, 100K, relay, virtual options and pacer roles, finishing at The Wreck Tiki Bar.

A 5K trail event at Chanco on the James in Surry County offering run, walk, and hike options along woods and the James River; online registration closes March 19 and race day registration is available.

A two-day women's trail festival in Williamsburg, VA with a competitive ten mile trail run plus an 8k and noncompetitive hikes, talks, and exercise classes. Proceeds support local charities and all finishers receive a medal and a T shirt.

A 5K run and walk at Appomattox River Regional Park in N. Prince George on April 11, 2026. All participants receive a medal and awards will recognize top overall and age group finishers; early registrants receive T shirts while sizes last.

Trail ultramarathon through nine trails in First Landing State Park, featuring marsh, forest, bay shoreline and a beach segment. Both 60K and 30K are cupless and include three aid stations and a 200 ml collapsible cup at pickup.

On May 16, 2026 at Bells Mill Park in Chesapeake the Strider XC Classic features a 5K cross country race, a competitive 5K race walk, and a 1.5 mile kids race, with one aid station, shirts for the first 150 registrants, and medals for all f..

A mostly trail half marathon at York River State Park with a new no frills Hike a Half format. The route mixes single track, fire road and a short paved section, includes aid stations and limited entries for a smaller field.

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.

Run for up to 10 hours on a 3.1-mile trail loop in Windsor Castle Park. Choose from shorter timed races or try the rucking option. All finishers get a handmade medal and there are awards for the top performers.

Pocahontas Trail Festival at Pocahontas State Park on October 4, 2026 offers a Half Marathon and a 10k on redesigned trail loops with chipped timing. Water stations are near miles 3, 6 and 9 and awards are given by age group.

This unique event challenges participants to run five consecutive 5K loops, one per hour, at Jockey's Ridge State Park. With individual and team options, runners must finish each loop within 55 minutes. The festive atmosphere includes music..

A 50K race and team relay on the Noland Trail at The Mariners' Museum Park in Newport News on November 7, 2026. The course is six laps and relay teams of two to six share the distance; participants also gain access to the fall festival.

A low-key trail event at Windsor Castle Park with 8-hour, 4-hour, and 10K options. Run or walk a marked 5-km loop with a stocked aid station, or try the rucking division. All finishers get a homemade medal, with awards for top performers.

A two-loop 50K trail run through First Landing State Park. Runners navigate a cupless course with two aid stations and an 8-hour time limit. All finishers get a medal, and a post-race party with pizza and drinks awaits.