Trail Running calendar near Woodbridge 2025-2026

Run a scenic 4k or 8k on the rolling grounds of Twisted Oak Farm Brewery in White Post, VA. Enjoy chip timing, a finisher medal, a tech shirt and a complimentary glass of beer, with a virtual option available.

Hit the scenic B&A Trail in Severna Park on March 29, 2026 with marathon and half marathon options, the marathon a Boston qualifier. Enjoy a mostly flat rails to trails route, generous aid, a finisher medal and participant apparel.

Run the Bull Run Run 50 Miler on April 4, 2026 in Clifton Virginia, a 50 mile trail through rolling forest and spring bluebells along the Bull Run Occoquan Trail. Civil War themed course, riverside views and a 13 hour cutoff.

Enjoy a scenic three loop 5k through Molon Lave Winery in Warrenton on April 4, 2026. Walkers and virtual runners welcome and finishers receive a winery glass, medal and tech shirt for a festive post race celebration.

Run an untimed 14 mile point to point along the scenic Dahlgren Railroad Heritage Trail in King George VA with shuttles. Enjoy playful aid stations with pie s'mores and doughnuts, support local charities and grab fun swag at the finish.

Join the Trail Demon 5k and 10k at Dirt Farm Brewing in Bluemont, VA on April 4, 2026, with in person or virtual entries. Expect technical forest trails, a finisher medal, tech shirt, chip timing and a post race beer.

Run the scenic Breeze Thru the Trees at Ruppert Nurseries in Gaithersburg, where a 5K and 1 mile fun run wind through a tree farm. Proceeds benefit the Montgomery County Children's Opportunity Alliance and early childhood programs.

Run to Remember at Piney Run Park offers scenic 5.25 mile loops with lake views and race options from a 5 Mile to 50K or the 8 Hour challenge scored by laps. Well stocked aid, swag and proceeds support youth programs and cancer research.

Run through scenic vineyard trails at Southern Revere Cellars on April 18, 2026 with 5k and 10k options and a virtual race. Enjoy a postrace glass of wine or beer while supporting Hooves & Paws Animal Rescue.

Run 3k or 6k through Barrel Oak Winery vineyards in Delaplane VA on April 19, 2026 for a rolling cross country experience. Enjoy a glass of wine, a medal and tech shirt while supporting Semper Fi and America's Fund; virtual and pet friendly..

Run 100 miles along the scenic C&O Canal towpath on April 25, 2026 near Knoxville, Maryland, with river and Appalachian views and helpful aid stations along the route. This spring ultramarathon is a WSER 2026 qualifier.

Run the Rock | Leesburg is a scenic 5K on gravel trails through an active rock quarry at Luck Stone. Finishers get a medal and shirt while proceeds benefit the Reeves Community Center; the event also features food, a raffle and family fun.

Run scenic trails at Third Winchester Battlefield with 5k, 10k and half marathon loops over light gravel and dirt. Chip timed with medals, technical shirts, on course aid and a virtual option, plus series points for racers.

Run three scenic laps around Bluemont Station Brewery & Winery in Bluemont, VA on April 26, 2026, and enjoy chip timing, a finisher medal, shirt, and a complimentary beer or wine. Walkers and virtual runners welcome.

Run the Muddy Shoes Farm Park Challenge at Agricultural History Farm Park on May 2, 2026, completing each lap in under one hour. Choose 3 hour, 6 hour, or 10 hour challenges or marathon and 25K; volunteers get event swag.

Tackle the Massanutten Mountain Trails 100, a 100 mile ultramarathon in Virginia's Shenandoah Valley with over 18,000 feet of climbing on rocky, rugged trails. You get 36 hours, live volunteer timing, well stocked aid and required GPS track..

Run scenic out and back courses along the C&O Canal towpath in Potomac on May 16, 2026, with 5k, 10k and half marathon distances. Enjoy chip timing, a tech shirt and finisher coin, support the EOD Warrior Foundation, or take part virtually.

Run a scenic, flat 5k along the Virginia Capital Trail by the James River at Rocketts Landing in Richmond. Choose in person or virtual entry, enjoy chip timing, a tech race shirt and finisher medal, with live results posted after the race.

Join the Night Raider at the Winery at Bull Run on May 22, 2026 for a festive evening 5k or 10k through scenic Manassas Battlefield trails. Enjoy chip timed results, a finisher medal, a technical shirt and a complimentary glass of wine.

The Old Dominion is a 100 mile loop through the Massanutten Mountains, offering rugged climbs and mixed road and trail terrain. Part of the Grand Slam of Ultrarunning, it runs June 6, 2026 with a 24 hour silver buckle cutoff.