Trail Running calendar near Leesburg 2025-2026

Run a flat, out and back 5k or 10k along Brunswick's scenic gravel path and support Wear Blue: Run to Remember. Finishers get a medal, technical shirt and a beer, with virtual options available for out of town runners.

Take on runnable hills, mud and possible snow on the Ranger Trail at Codorus State Park with 8 Miler, 25K or 50K loop options. Presented by York Road Runners Club, the race benefits a local animal rescue and offers prizes and swag.

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.

Join Washed Clean on March 28 at Genesis Church in York for a fun trail run or walk that finishes with a foam celebration and a free kids fun run. Family friendly and charity focused, register early for a free t shirt and water bottle.

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.

Take on 50 miles of forested, rolling trail along the Occoquan River and Bull Run in Clifton, Virginia, featuring sweeping bluebell stands and a Civil War themed route. Enjoy a team competition, Trail Sisters approval, inclusive awards and..

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.

Hit the forest trails behind Dirt Farm Brewing for the Trail Demon 5k or 10k with beer, medals and chip timing on April 4, 2026. Run in person or virtually and support Boulder Crest Foundation serving veterans and first responders.

Run a scenic, untimed 14 mile point to point on the Dahlgren Railroad Heritage Trail in King George, VA. This flat, fun trail raises funds for local charities, sells out fast, and finishes with tasty treats and handy swag.

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 rugged trails with creek crossings and climbs at Buck Ridge Burn in Pine Grove Furnace State Park on April 12, 2026. Choose a half marathon, 10K, 5K or virtual option and enjoy small fields, handmade medals and a finisher coaster.

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.

Enjoy a scenic chip timed 5k atop Hauser Hill, through orchards and ridge top trails in a cross country style course. Finishers receive a tee, collapsible wine glass and a medal that doubles as a wine stopper with a pour included.

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..

The C&O Canal 100 is a scenic 100 mile ultramarathon along the Potomac on the C&O Canal towpath, starting and finishing at Camp Manidokan on April 25, 2026. Expect smooth low elevation terrain, reliable aid stations and a Western States qua..

Run the Rock Leesburg is a unique trail 5K inside an active rock quarry at Luck Stone, with gravel terrain and scenic views. Family fun, finisher medals and proceeds support the Reeves Community Center Foundation.

The Winchester Battlefield Half will take place in Winchester on Saturday 25 April 2026. You can run between 5 and 21 kilometers.

Lace up for the Bluemont Station Brewery and Winery 5k on April 26, 2026, a three lap cross country run around scenic winery grounds with some rolling hills. Walkers are welcome and a virtual option lets you join from anywhere.

Run scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.