Trail Running calendar near Leonardtown 2026-2027

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.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 20 May 2026. You can run between 10 and 40 kilometers.

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 Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 27 May 2026. You can run between 10 and 40 kilometers.

Take on the Taskinas Creek Half Marathon at York River State Park, a trail friendly 13.1 mile hike or run with rolling single track and a tough final two miles. Limited to 250 entries, medals and PR coaster awards await finishers.

Tackle the OSS/CIA 50 Mile Night Run in Prince William Forest Park with 50, 25 or 10 mile options under the stars. Enjoy single track trails, stocked aid stations and a scenic loop run twice for the 50 mile.

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.

Get muddy and fast at MCRRC XC on the Farm, a fun 5k cross country at Agricultural History Farm Park in Derwood on June 28, 2026. Open to all ages with affordable registration and a relaxed club atmosphere.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

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.

Run scenic, moderately technical trails at Schaeffer Farms in Germantown, starting and finishing at the Button Farm Living History Center. Choose a 5K or 10K for a rooty, stream crossing adventure while supporting local charities.

Tackle twisty single track and rolling hills at Little Bennett Regional Park in the Blue Crab Bolt Trail Run, offering 5K and 10K options on scenic, streamside trails. Optional donations benefit Interfaith Works for local families.

Run rugged single track and river crossings at MD Heat Trail Race in Patapsco Pickall, Elkridge MD. Choose 25K or 50K and expect big climbs, technical rock sections, helpful aid stations and a finish with food and beer.

Enjoy a scenic trail 5k or 10k through Leopold's Preserve in Broad Run, Virginia on Aug 23, 2026, with chip timing, medals and a tech shirt. Walkers and virtual participants are welcome and races earn points toward year long series.

Run through Creekside Farm on scenic dirt trails along the Rappahannock River with 5K and 8K options, chip timing and awards. Celebrate after with live music, craft beer, a free pint for entrants 21 plus and food trucks.

Push your limits at the Pemberton 24, a 24 hour running challenge at Pemberton Park in Salisbury MD on September 18 to 19, 2026. Run hourly 5K loops solo or with a four person team, rest at your camp, and chase points and nightly bonuses.

Run with your dog at the Howlin' Coyote Canicross Trail Race in Caledon State Park, featuring varied terrain and a 10 km canicross plus a one mile Wild Pup dash. This non profit event supports Friends of Caledon and is disposable cup free.

Take on scenic new trails at Pocahontas State Park with a chip timed half marathon or 10K. Expect runnable singletrack, on course water stations, live results and race day age group awards in a festive park setting.

Experience scenic, historic trails of Patapsco Valley State Park with the 50K and 25K on Oct 24, 2026, offering in person and virtual options. Finishers earn special swag including a hand thrown mug for 50K completers.

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..