Trail Running Calendar Virginia 2025-2026

Challenge yourself at the Seven Trails Ultra Festival in Damascus VA, November 14 to 16, 2025. Run a scenic 7.7 mile loop with chip timing and live tracking; choose 25K or tackle 100 miles to earn a handcrafted buckle.

Run through the vineyards at Barrel Oak Winery in Delaplane VA on November 15 with 3k and 6k options on a rolling cross country loop. Finishers enjoy a glass of wine, a medal and tech shirt plus chip timing and awards.

Join a friendly group run along the Festivus loop on Middleburg's Sandridge Trail. This 7.2 mile course preview offers a welcoming community pace and a great way to learn the route and meet fellow runners.

Join the Fall Backyard Burn at Hemlock Overlook for scenic trail running along Bull Run with roots, rocks and stream crossings. Choose 5.2 or 9.5 miles and enjoy aid stations, race swag and a lively finish.

Join the Freeze Your Gizzard 5K or 1 Mile on Nov 22 at Ida Lee Park in Leesburg for a scenic but challenging cross country course and lively community vibe. Pre registered 5K runners receive a long sleeve shirt and the event supports Loudou..

Event details The 2025 Herndon Turkey Trot is a cross-country style 5K held on November 22 at the Herndon Community Center, 814 Ferndale Ave., Herndon, VA. The race is open to participants age 4 and up. Runners must complete the 5K in 45 mi..

Run a scenic fall trail through Manassas National Battlefield from The Winery at Bull Run with 5k and 10k options, in person or virtual. Enjoy a postrace glass of wine and a finisher medal while supporting the Manassas Battlefield Trust.

Celebrate the 30th Chesterfield Alumni Run on Thanksgiving at Pocahontas State Park with a free community XC 5k and kids fun run with gingerbread cookies. Stay for giveaways and optional donations to support local track and cross country.

Join the DPS Education Foundation Turkey Trot on Thanksgiving Day in Danville for a scenic 5K along the Dan River plus a children's fun run. Run or walk to support DPS students and teachers while enjoying the Riverwalk Trail.

Celebrate Thanksgiving at the Lake Anna Turkey Trot on November 28, 2025 at Lake Anna State Park. Run a 5k, 10k or half marathon on scenic trail and road courses with a tech shirt, finisher medal and chip timing, or join virtually.

Run the After Ate 8K and 2 Mile in Williamsburg on Nov 29, featuring chip timed races, competitive walk and ruck options, and a custom long sleeve shirt. Finishers get pizza, a local beer and a chance to support a community food drive.

Devil Dog Ultras in Prince William Forest Park offers 50K, 100K and 100 mile trail loops on well marked single track and rolling fire roads. Expect staffed aid stations, limited bunkhouse beds and a lively winter ultrarunning weekend.

Run the Freight Train on Saturday December 6 2025 in Farmville Virginia, with distances from half marathon to 100K on a scenic rail trail. Cross the iconic High Bridge twice and earn a handcrafted pottery finisher award.

Run the flat, scenic High Bridge rail trail from Farmville in the Freight Train Ultra Marathon with half marathon, 50K and 100K options. Expect exposed bridges and open trail, friendly aid stations, and a festive finish at the historic Trai..

The Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm tr..

Trail run at Fountainhead Regional Park around the Occoquan Reservoir with a 4.8 mile loop and a 10.5 mile option. EX2 Adventures provides on course aid, post race food and swag and a kids race supporting Homestretch.

Join the Tidewater Strider Dismal Swamp in Chesapeake VA on Dec 7, 2025 for 50K, marathon, half marathon, relays and a walkers option on scenic out and back looped trails. Aid stations, finisher apparel and post race pizza and beer await.

Run the Pocahontas 5k, 10k or half marathon on Dec 13 along the scenic Bright Hope Trail in Pocahontas State Park. Walkers and virtual runners welcome with chip timing. Finishers get a coin and shirt and proceeds benefit Operation Turbo.

The Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain wit..

Join a free 17 mile run along the scenic Virginia Creeper Trail from Alvarado Station to Abingdon. Handmade mementos for top, middle and final finishers plus warm post race drinks and snacks.