Trail Running calendar near Leonardtown 2025-2026

Run For Your Life 5k is a cross-country 5K Run/Walk held at Verdun Adventure Bound in Rixeyville, Virginia (17044 Adventure Bound Trail). The race takes place on Verdun’s cross-country course across a 67-acre woodland setting, offering a true 5K course suitable for runners and walkers. The event fea..

Greensprings 24 is a 24-hour endurance race held in Williamsburg, Virginia, at the Greensprings venue (3751 John Tyler Hwy). The course is a USATF-certified 2.215-mile loop on crushed gravel, mostly flat and scenic, with a non-technical profile. Runners can complete full loops to reach targets such..

Patapsco Valley 50K is an annual ultramarathon held near Baltimore, MD, with race headquarters at CCBC-Catonsville. The in-person event offers a 50k and a 25k, plus virtual options, set on a scenic, historic, well-marked trail course through Patapsco Valley State Park. The race features five aid sta..

RTB Fair Winds 5k/Fun Run is held at Quiet Waters Park in Annapolis, Maryland. The event offers a 5K, a Fun Run, and a Virtual 5K/Fun Run option. Runners traverse a fully paved course through woods and meadows, presenting a scenic park setting.The atmosphere is upbeat and community-minded, with cost..

The Halloween Horror 10k is a trail running event held at Conway Robinson State Forest in Gainesville, Virginia. The race features a challenging loop course through forest trails with some technical terrain and minor hills, with the 10k consisting of two laps of the 5k route. Participants receive a..

EX2 Adventures' Fall Backyard Burn Trail Run at Riverbend Park in Great Falls, VA offers 5-mile or 10-mile trail options along the Potomac River just west of Great Falls National Park. The course features riverside singletrack, a few short hills, and non-technical terrain with scenic views; elevatio..

The MCRRC Stone Mill 50 Mile Run is a 50-mile trail ultramarathon in Montgomery Village, Maryland, organized by MCRRC. The course uses forested, rolling terrain along the Seneca Greenway and Muddy Branch trails in Montgomery County, primarily on single-track dirt trails with small stream crossings...

EX2 Adventures’ Schaeffer Half Marathon and 10K Trail Run takes place at Button Farm Living History Center in Germantown, MD, on Schaeffer Farms. The course features Schaeffer’s renowned twisty singletrack and open farm-field segments, offering a rugged mix for trail runners. Distances include a hal..

Rosaryville Veterans Day Trail Race, held in Rosaryville State Park in Upper Marlboro, Maryland, offers 50K and 20K trail distances on wooded perimeter single-track trails. The course features rolling hills with about 2,600 feet of elevation gain, mostly through deep woods and meadows, with scenic v..

Talaria Trail Run is a fall trail event held at Trap Pond State Park in Laurel, Delaware. It features a 4.5-mile Race and a 2-mile Walk. The course follows the Bob Trail—a 4.5-mile loop around the 90-acre Trap Pond—winding through hardwood forests, crossing a dam at Raccoon Pond, and spanning boardw..

Fall Backyard Burn at Hemlock Overlook is part of EX2 Adventures’ Fall Backyard Burn Trail Running Series. Held at Hemlock Overlook, Clifton, Virginia, the event offers 5-mile and 10-mile trail courses. Elevation gains are about 600 feet for the 5M and 1,200 feet for the 10M.The courses traverse Bul..

Freeze Your Gizzard 5K and 1 Mile is held at Ida Lee Park in Leesburg, Virginia. Celebrating 23 years of running, this cross-country event offers a 5K through Ida Lee Park’s 138 acres and a 1-Mile Fun Run, starting and finishing near the park’s Gazebo. The course features uneven terrain and steep hi..

The Tuckahoe 25k is a trail race in Queen Anne, Maryland. It covers 25k (about 15.5 miles) on mostly single-track trails with some wider horse trails. The course is not overly technical but includes runnable hills, rooty, muddy sections, and varied conditions.Runners can expect three fully stocked a..

Fall Backyard Burn Trail Run – Laurel Hill is a trail race at the Workhouse Arts Center in Lorton, Virginia, on Lorton Reformatory grounds. The course blends forested and open meadow singletrack across 1600 acres, mostly dirt and crushed stone with short pavement at the start and finish. There are n..

The Winery at Bull Run Turkey Trot offers a scenic trail 5k and 10k through the Manassas National Battlefield Park, starting and finishing near The Winery at Bull Run in Centreville, VA. The course is a cross-country style route across battlefield trails, including dirt paths, a boardwalk, and grave..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

The Lake Anna Turkey Trot Half is a scenic and challenging running event held at Lake Anna State Park in Spotsylvania, Virginia. It features three race distances: a 5k trail run, a 10k that is half trail and half paved road, and a half marathon with a similar mixed course. Walkers are welcome, and t..

Now in its 27th year, the Milford Cross Country Booster Reindeer Stampede 5k takes place at Killens Pond State Park in Felton, Delaware. The event offers a 5k run/walk and a competitive walking option, benefiting Milford High School Cross Country. The course, mapped in advance, emphasizes a family-f..

The Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm trails, pastures, woods, and gravel roads, with uneven terrain..

Devil Dog Ultras is a trail ultramarathon in Prince William Forest Park, VA. It offers 100-mile, 100K, and 50K loops on trails with roots and rocks, plus fire roads. The first loop is 23 miles; subsequent loops are 19.5 miles.The 50K is one loop plus a 9-mile extension; the 100M runs five loops and..