Trail Running calendar near Chesapeake 2025-2026

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 l..

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..

Event Greensprings 24 is a 24-hour endurance race on Saturday, October 25, 2025, in Williamsburg, VA (3751 John Tyler Hwy). The event benefits The Arc in Williamsburg, VA. Awards are given for completing 50k, 50 miles, 100k, 75 miles, and 1..

Celebrate Halloween on the trails of First Landing State Park with Haunts and Hallows half marathon. Expect sandy sections, roots, friendly aid stations, finish line donuts and a finisher beanie in a welcoming community vibe.

Event overview The Indian Fields Tavern/5 Fields Brewing Co. Low Key Halloween Haunts takes place on Sunday, October 26, 2025, in Charles City, Virginia. The event offers two distances: 5k 10k The published entry fee is $20. The entry inc..

Take on the scenic Noland Trail 50K in Newport News at Mariners Museum Park, solo or as a 2 to 6 person relay over six laps. All finishers get a shirt and medal and registration includes the Fall Festival with live music and craft beer.

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-certifi..

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..

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 w..

Event The Snowy Owl 10 Mile takes place on Sunday, January 4, 2026, at York River State Park in Williamsburg, VA. The event distance is 10 mile and it benefits AWARE (Alliance of Wild Animal Rehabilitators and Educators). The event uses a s..

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 t..

Event overview The Swammie Shuffle 200 is a long-distance running event in Virginia Beach, VA on February 22, 2026. The event is an out-and-back course of about 200 miles that sends runners south through the Outer Banks of North Carolina to..

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 i..

Join the Women's Trail Festival at Freedom Park in Williamsburg for scenic 10 mile and 8k trail runs, fitness classes, talks, lunch and a social with wine and beer. Community focused with awards for competitive races and proceeds benefiting..

Explore maritime forest, cypress swamps and Broad Bay shoreline at the Long Creek 60k in Virginia Beach on April 19, 2026. Pick 60K or 30K, tackle scenic trail loops and earn a custom finisher award when you finish within the time limit.

Take on the Virginia Run for Cancer, a 24 hour solo and team event on a flat 3.75 mile all dirt loop in Hampton. Walkers welcome and volunteers support runners while the event raises funds for the American Cancer Society.