Trail Running calendar near Chesapeake 2026-2027

Enjoy a scenic 5K through the OBX maritime forest in Kitty Hawk on Feb 16, with a cozy community vibe and a mix of gravel and soft trail underfoot. All proceeds benefit local student runners.

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..

Run Blackbeard's Revenge 100 Ultra and Relay across the scenic Outer Banks from Corolla to Hatteras with solo and relay entries on a paved coastal route. Expect aid stations, a finisher medal or 100 mile buckle and a finish at The Wreck.

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.

Experience the Women's Trail Festival in Williamsburg, a two day event with technical 10 mile and 8k trail options for racers or hikers. Enjoy clinics, classes, a finisher medal and community giving that supports local charities.

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.

Run loops around scenic Windsor Castle Park in Smithfield, VA with timed options from a one lap 5k up to 10 hours. Rucking is welcome for the longer events and a stocked aid station plus homemade finisher items make this a low key, supporti..

Take on scenic new trails at Pocahontas State Park with a chip timed half marathon or 10K. Expect runnable singletrack, on course water stations, live results and race day age group awards in a festive park setting.

Run five hourly 5K loops for a cumulative 25K at Jockey's Ridge State Park, including a dune crossing and team relay options. Chip timing, finisher medal and a festival vibe with food, music and beach access make this a fun fall challenge.

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.

Get Outside 8 Hour at Windsor Castle Park offers solo and team options on a scenic 5K loop with timed formats from 8 hours to 5K. Ruck entries carry 10 pound packs, the course is chip timed, and all finishers get a homemade medal.

Run a scenic 50K two loop course at First Landing State Park in Virginia Beach on December 13, 2026, with aid stations and a lively finish. Finishers get a Brooks shirt and medal and can celebrate at a brewery party.