Trail Running calendar near Leonardtown 2026-2027

Trail races at Cromwell Valley Park include 25k, 12.5k and a family 5k with mile-marker activities. Proceeds benefit the Gunpowder Valley Conservancy, Cromwell Valley Park and TALMAR.

A Mother's Day 5k and 10k in Silver Spring, Maryland, held by Swift Running with a course that passes through Martin Luther King Jr. Recreational Park. The event offers in person and virtual entries with tiered registration fees.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

Three trail races in Richmond across Belle Isle and the James River waterfront: a chip timed 5K, a 10K through riverfront trails, and a 13.1 mile urban single track half marathon with riverbank terrain and skyline views.

A towpath race at Carderock Park in Potomac, MD on May 16, 2026, offering 5K, 10K and half marathon distances; courses are described as fast and flat, walkers are welcome, and virtual entry options include medal and shirt choices.

Run for a cause on the scenic Virginia Capital Trail at the Motion for Justice 5K. This flat, paved course offers views of the James River and includes chip timing, a finisher medal, and a tech shirt. Awards recognize top overall and age gr..

Test your resilience in this 24 hour endurance challenge in Annapolis. Set your own mileage goals to honor military heroes while enjoying provided meals and a community trail running environment.

A trail-focused, approximately 10 km scramble along the James River with roots, gravel and low-hanging branches. Self-serve cup-less water stops require personal hydration; wave starts are used and prizes go to the top three overall finishe..

A roughly 13.1 mile trail half marathon along the James River in Richmond, featuring single track, bridges and riverbank scenery. Wave starts control trail volume; entries include a finisher shirt and chip-timed bib.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

An evening 5 km and 10 km run through the historic Manassas National Battlefield with start and finish at The Winery at Bull Run in Centreville, VA. In-person and virtual entry options are available.

Furbutt's Backyard uses a 4.167 mile hourly loop with a 24 Hour 100 mile limit and a 12 Hour After Dark option at Mustang Trailhead. A single aid station supplies water, ice, Gatorade and snacks and crews are allowed there.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

A 100-mile, 10-loop event on Rock Creek Trail near Washington D.C., with about 8,200 ft total elevation and a 36-hour cutoff. Two ticket types are listed at the same price including tax.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

A community team race at Burke Lake Park on June 6, 2026 featuring a 5K race and a 2K walk and roll that raises funds for services and advocacy for people with intellectual and developmental disabilities.

A mostly trail, low frills half marathon at York River State Park on June 7 2026 with a new Hike a Half option, marked trails, aid stations, and a five hour time limit.

Trail Trotters 5K & Fun Run at Promise Landing Farm in Upper Marlboro offers a farm-trail 5K and a fun run to support the farm's riders and programs. The event includes free parking, a shirt deadline of May 16, no pets, and refunds up to se..

A night trail event in Prince William Forest Park featuring a 50 mile race made of two 25 plus mile loops, plus 25 mile and 10 mile options. The course is mostly single track with staffed aid stations and defined crew and pacer rules.

A chip timed 5k at Corteau Vineyards in Mechanicsville, Maryland on June 13, 2026, featuring vineyard scenery, a t-shirt, collapsible wine glass, finisher medal that doubles as a wine stopper, and an on-site wine pour.