Trail Running calendar near Delaplane 2025-2026

Join the scenic Seneca Creek Greenway Trail in Gaithersburg MD on March 7, 2026 for a marathon or an extended 50K. Run single track parkland trails and choose to finish at the marathon or keep going to complete the 50K.

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.

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.

Tackle a 41 mile trail ultra in the Shenandoah Valley with about 8,000 feet of climbing, waterfalls and dramatic cliff overlooks. Limited to 125 runners, this remote loop offers aid stations and a 13 hour 15 minute cutoff.

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.

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 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.

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.

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.

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.

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.

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..