Trail Running calendar near Leonardtown 2026-2027

A cross country 5k and 10k at Wilderness Run and 1781 Brewing in Spotsylvania on February 14, with on-course water stations, chip timing, finisher awards, a virtual option, and proceeds benefiting Semper Fi and America’s Fund.

Kick off the running year with this historic 5k at Kinder Farm Park. The mostly flat trail course features two gentle hills and is the first event in the Annapolis Striders Championship Series. Remember to bring your own water, as hydration..

This trail 5k runs through the forested paths of the Wicomico Demonstration Forest in Parsonsburg. It's the inaugural race on this trail, supporting the 4STEPS Therapeutic Riding program. All proceeds fund therapeutic riding services for th..

Trail races in Columbia, Maryland along the Little and Middle Patuxent Rivers, offering 5K, 10K and half marathon distances with start and finish at the Guilford Pratt Truss Bridge. Registration includes a long sleeve shirt, finisher medal..

A club-based 10 miles race in Columbia, MD where runners score points for their RRCA club; awards are given by club and the event is part of the Maryland RRCA Grand Prix series.

Trail 5k and 10k races at Paradise Springs and Hemlock Overlook Park with series points, chip timing and a post race glass of wine. The 10k is two laps of the 5k technical route with multiple water stations.

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

Trail races of 5 Miler, 10 Miler and a two person 10 Miler relay take place at Rockburn Branch Park in Elkridge on March 1, 2026; a portion of proceeds supports Bigfoot Endurance for Parkinsons research.

On March 1, 2026 at Wakefield Park in Annandale, the Spring Backyard Burn offers 5.5 mile and 10 mile trail race options across singletrack, doubletrack, stream crossings and minimal pavement. The event features aid stations, post race food..

A 31 mile trail event at Rockburn Branch Park in Elkridge Maryland featuring six loops of about 5.179 miles. Relay teams of two to six can share the distance and an aid station is stocked with food and drinks.

A women only trail endurance event near Triangle VA offering 50K and 25K options, two roughly 15 mile loops, five aid stations, and a limited field with a 9 hour cut off.

Tackle forest trails on a two lap loop at Conway Robinson State Forest. This winter 10k offers series points, a technical shirt, and supports pet rescue. Walkers are welcome, and a virtual option is available.

Trail marathon and 50K on March 7, 2026 at Seneca Creek State Park near Gaithersburg, MD. Runners may stop at the marathon finish or continue to complete the 50K, and entries include a tech shirt and finisher medal.

A free International Women’s Day endurance day at Beaverdam Reservoir Park featuring a 7.5-mile loop and varied trail surfaces. The event centers women, offers course support through sunset, and focuses on movement and mutual support.

A 10 mile trail race in Pocomoke State Forest on March 15, 2026. The event is cupless with one aid station, limited parking, and packet pickup available the day before.

A trail race at the Workhouse Arts Center in Lorton on March 15, 2026, offering mostly singletrack through forest and meadows with options of roughly 5.4 miles or 10 miles. The event includes aid stations, optional medals, a kids program, a..

A cross-country 5K and 1 Mile run at Wilderness Run Vineyards in Spotsylvania on March 21, 2026, featuring trail hills, on-site parking, a food truck and live music, drink tickets for adults, a 50/50 raffle, and awards across multiple age g..

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

A two-day women's trail festival in Williamsburg, VA with a competitive ten mile trail run plus an 8k and noncompetitive hikes, talks, and exercise classes. Proceeds support local charities and all finishers receive a medal and a T shirt.

Trail races at Rosaryville State Park in Upper Marlboro MD on March 28, 2026 include half marathon, 10K and 5K plus virtual options. Courses run through hardwood forests, fields and equestrian trails with multiple aid stations.