Trail Running calendar near Leonardtown 2025-2026

Take on scenic forest trails at Conway Robinson State Forest with a 5k or two lap 10k, suitable for runners and walkers of all levels. Support the Lost Dog & Cat Rescue Foundation and earn a finisher coin plus a tech shirt.

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.

Explore a scenic 10 mile trail through laurel and pine in Pocomoke State Forest along Blades Road, with mossy singletrack and creek crossings. Bring your own cup or bottle as the race is cupless and offers one aid station.

Join the Women's Trail Festival, a two day trail weekend at Freedom Park in Williamsburg with 10 mile and 8k options plus social hours and educational talks. All finishers earn a medal, proceeds benefit local charities and the event is Trai..

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.

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 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 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.

Run the Dash Through the Dirt May 16, 2026 at Carderock on the scenic C&O Canal towpath in Potomac MD. Choose 5k, 10k or half marathon on light gravel with chip timing, tech shirt and finisher coin. Proceeds benefit EOD Warrior Foundation.

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.

Run or hike the Taskinas Creek Half at York River State Park on June 7, 2026. This no frills trail event features rolling, rugged terrain and is limited to 250 entrants, with finisher medals and a special PR award for faster finishers.

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, with 50 mile, 25 mile and 10 mile options on scenic single track and fire roads. Expect rugged trails, moonlit views and well stocked aid stations.

Run scenic single track trails at the Blue Crab Bolt Trail Run at Seneca Creek State Park on June 27, 2026. Choose a 5K or 10K and enjoy woods, lake views and streams as the kick off to the Blue Crab Bolt series.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.