Trail Running calendar near Leonardtown 2025-2026

We have found 56 Trailruns within 80 miles of Leonardtown. See below where and when you can find the races.

The DHRT 50K is an exciting trail running event set in King George, Virginia, taking place on August 2, 2025. This challenging race traverses the scenic Dahlgren Railroad Heritage Trail, offering participants a flat and well-maintained course primarily shaded by trees. Runners will face the added ch..

The Dahlgren Heritage Rail Trail 50K is a scenic trail race held in King George, Virginia, on August 2, 2025. Participants will run on the flat, well-maintained Dahlgren Railroad Heritage Trail, which features mostly shaded, solid footing surfaces like dirt, grass, and crushed stone. The course is a..

The 3H Trail Half Marathon, scheduled for August 2, 2025, in King George, VA, offers participants a scenic out-and-back course along the Dahlgren Railroad Heritage Trail. This flat and smooth trail, ideal for running, features a variety of surfaces and is shaded by trees, providing a comfortable env..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running options of 25K and 50K distances. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and a s..

The Terrible Twelve is a 12-hour self-supported trail running event held at the Warhill Nature Trail in Williamsburg, Virginia. Participants run or walk as many 3.7-mile loops as possible on a crushed gravel course featuring rolling hills and scenic views, though personal lighting is required for ni..

September 2025

The VHTRC Women's Half Marathon will take place in Fairfax Station on Saturday 13 September 2025. You can run between 7 and 13 miles.

The 12 Hour - Adventure Trail Run is an endurance event held at Prince William Forest Park near Triangle, VA. Participants run on a 6.5-mile looped trail course featuring single track, fire roads, and varied terrain with hills, rocks, roots, and mud. The event challenges both novice and experienced..

The Pemberton 24 is a unique 24-hour running event held in Salisbury, Maryland, featuring a series of 5K trail runs in The Pemberton Park trail system. Starting Friday evening, a 5K race begins every hour on the hour for 24 hours, allowing participants to run as many 5Ks as they choose, either solo..

The Brandy Station Battlefield 10k and 5k is a scenic trail race held at the historic Brandy Station Battlefield in Virginia. Participants can choose between a cross-country 10k or a 5k gravel dirt road course, with some elevation gains. The event features chip-timed results, finisher medals, and te..

October 2025

The Pocahontas Trail Festival is a running event taking place at Pocahontas State Park in Chesterfield, Virginia. Scheduled for October 5, 2025, the festival features a Half Marathon and a 10k race, both designed to showcase the park's scenic trails. Participants will enjoy professionally timed race..

The Full Distance 10k and 5k is a scenic trail race held at Locust Shade Park in Triangle, VA. Participants can choose between a 5k or 10k course, with the event featuring chip timing, finisher medals, and technical event shirts. The course includes trail segments with some roots and hills, and wate..

The Wilderness Run 10k is a scenic cross-country race held at Wilderness Run Vineyard near the historic Chancellorsville and Wilderness battlefields. The event features both 5k and 10k courses with hills and trail terrain, offering a challenging and picturesque experience. Participants receive a fin..

The Fall Backyard Burn Trail Run at Lake Fairfax Park in Reston, VA, offers runners a scenic and challenging experience on a 5.1-mile singletrack course with minimal pavement and about 300 feet of elevation gain per lap. Participants can choose to run one lap (5 miles) or two laps (10 miles), with t..

The Patapsco Valley 50K is an annual ultramarathon held in Baltimore, Maryland, at Patapsco Valley State Park. The event features a scenic, well-marked trail course with options for 50K and 25K distances, including virtual categories. Runners receive high-quality event shirts, finisher awards, and e..

The Greensprings 24 is a 24-hour endurance race held in Williamsburg, VA, starting on October 25, 2025. Participants can run, walk, or crawl on a scenic, flat, crushed gravel loop course, with each loop measuring 2.215 miles. The event encourages runners to reach personal milestones such as 50 miles..

The Halloween Horror 10k is a trail running event held at Conway Robinson State Forest Park. Participants can choose between a 5k or 10k race, with the 10k being two laps of the 5k course. The course features forest trails with technical terrain and minor hills.Runners receive a finisher’s medal, a..

November 2025

The Fall Backyard Burn Trail Run at Riverbend Park in Great Falls, VA, is a scenic trail running event held on November 2, 2025. Participants can choose between 5-mile (one lap) and 10-mile (two laps) courses featuring beautiful riverside singletrack trails, gentle hills, and stunning views along th..

The MCRRC Stone Mill 50 Mile Run is a challenging trail running event set in Montgomery County, Maryland, showcasing the scenic Seneca Greenway and Muddy Branch trails. Participants navigate a primarily single-track dirt course featuring forested terrain and small stream crossings, with some areas p..

UTMB Index

The Schaeffer Half Marathon and 10K Trail Run, organized by EX2 Adventures, takes place at Button Farm in Germantown, Maryland. The course features twisty singletrack trails and open farm fields, offering a scenic and challenging experience for runners. The half marathon covers approximately 13.3 mi..

The Rosaryville Veterans Day Trail Race, held annually in Upper Marlboro, Maryland, features 50K and 20K trail races through Rosaryville State Park's scenic wooded trails and meadows. The event celebrates veterans and offers a challenging yet accessible course with rolling hills, mostly single-track..