Trail Running calendar near Chesapeake 2025-2026

Hosted by the Association of the United States Army Southern Virginia Chapter, the Southern Virginia 5K offers a 5K Run/Walk and a 10K Run/Walk along the Capital Trail in Charles City, Virginia. The course runs on the scenic Capital Trail with options for all paces. The event takes place at 9220 Joh..

The Pocahontas Trail Festival is a trail running event held at Pocahontas State Park in Chesterfield, Virginia. It features a Half Marathon and a 10k race, both starting and finishing on a large grass field near the park's boat launch. The course was redesigned to emphasize trail running, incorporat..

Another Round 25K takes place at Jockey’s Ridge State Park in Nags Head, North Carolina. The event comprises five 5K loops, totaling 25 kilometers; runners can go solo or pair up as a two-person team. Each loop is run on the hour, and all loops are chip-timed, with final results based on cumulative..

The Smithfield Hog Jog is an annual 5K run and walk held at Windsor Castle Park in Smithfield, Virginia. The event features a 5K race with chip timing and a Kid's Piglet Run, where all young participants receive awards. The race welcomes up to 500 participants and offers awards across various age gr..

Greensprings 24 is a 24-hour endurance race held in Williamsburg, Virginia, at the Greensprings venue (3751 John Tyler Hwy). The course is a USATF-certified 2.215-mile loop on crushed gravel, mostly flat and scenic, with a non-technical profile. Runners can complete full loops to reach targets such..

Haunts & Hallows is a half marathon trail race held in Virginia Beach, VA, at First Landing State Park. The course features gently rolling trails with about 300 feet of elevation gain, including roots, bridges, and sandy sections, offering scenic and varied terrain. The event fosters a supportive co..

The Noland Trail 50K & Relay is held in Newport News, Virginia, on the scenic Noland Trail at The Mariners’ Museum Park. Location: 100 Museum Drive, Newport News, VA 23606. The event offers a solo 50K and a 2–6 person relay.The 50K route consists of six laps on the trail, with a short section added..

The Tidewater Strider Dismal Swamp 50K/Marathon/Half Marathon/50K Relay takes place in Chesapeake, Virginia. The event offers five options: Dismal Swamp 50K, Marathon, Half Marathon, 50K Relay, and a Half Marathon Walkers. The USATF-certified courses are described as fast: the 50K is four loops of a..

The Pocahontas Half is a scenic running event held at Pocahontas State Park near Richmond, Virginia. It features a half marathon, 10k, and 5k race, all taking place on the forested Bright Hope Trail, which offers a soft dirt and pine needle surface with some minor hills. The half marathon course is..

Mel Williams Memorial Seashore 50K presented by Brooks is a two-loop trail ultramarathon at First Landing State Park in Virginia Beach, starting and finishing at the Narrows boat ramp on 64th Street. The 50K distance is run on park trails with aid stations at 64th Street and Bald Cypress, providing..

The Snowy Owl 10 Mile is a trail running event held at York River State Park in Williamsburg, VA. The course features a mix of technical single-track trails, dirt fire roads, a short paved downhill finish, and scenic boardwalk sections, covering 10 miles with about 600 feet of elevation gain. Runner..

Chills In The Mill: Harwoods Half Marathon & 5K takes place in Yorktown, Virginia, starting off Oriana Road near Harwoods Mill. The event offers two distances — Harwoods Half and Harwoods 5K — with capped fields (200 for the half, 150 for the 5K). Runners encounter a mix of wide, open trail roads an..

Swammie Shuffle 200 is a 200-mile, self-supported ultramarathon based in Virginia Beach, Virginia. Runners depart from Sandbridge Beach and travel south through the Outer Banks of North Carolina to the Cape Hatteras Lighthouse, then turn around for the return trip to finish along the Virginia Beach..

Blackbeard’s Revenge 100 Ultra & Relay is a North Carolina Outer Banks endurance event running from Corolla to Hatteras. Scheduled for March 21–22, 2026, it offers 100 miles, 100K, and a 100-mile relay for teams. The point-to-point course is 100% paved, with sweeping coastal views and the Outer Bank..

Women's Trail Festival is a trail running and hiking event in Freedom Park, Williamsburg, Virginia, organized by Happy Cat Fitness. The festival features a competitive 10-mile loop on Saturday and a 10-mile hike on Sunday, plus an 8k hike on Saturday that uses the first portion of the course. The lo..

Long Creek 60k/30k takes place in Virginia Beach, VA, within First Landing State Park. The course covers all nine scenic trails: Long Creek, White Hill Lake, Cape Henry, Kingfisher, Osmanthus, Bald Cypress, High Dune, Fox Run, and Osprey. Runners traverse maritime forests, cypress swamps, salt marsh..

Virginia Run for Cancer is a 24-hour running event in Hampton, Virginia at 1255 Big Bethel Road. It offers 24-hour solo and team formats with a 3.75-mile flat dirt nature park trail lap that participants complete repeatedly. The course is USATF-certified (VA12075RT) and walkers of all abilities are..