Trail Running calendar near Leonardtown 2025-2026

Event details The Full Distance 5k & 10k takes place on October 11 at Locust Shade Park. Points from the event count toward the Year-Long 5k, 10k and Back of the Pack Series and the Sippin Series. A virtual race option is offered. Walke..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. T..

Coastal Walk & 5K Run is a charity running and walking event held at Assateague State Park in Berlin, Maryland, located at 6915 Stephen Decatur Highway. Organised to support Coastal Hospice, it offers two options: a Coastal Hospice 5K Run a..

Event The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series...

2025 Wilderness Run 5k & 10k The event takes place on October 18 at Wilderness Run Vineyard in Spotsylvania, VA (11109 Plank Rd; GPS 38.325153, -77.719921). It features cross country trail courses with hills. The 5k is an out-and-back o..

The 22nd Annual Mariners Bethel 6.2m & 3.1m Trail Run takes place at Camp Barnes in Frankford, Delaware. The flat, fast course begins and ends at Camp Barnes, winding through cross-country roads and trails in the Assawoman Wildlife Refuge...

Run the Fall Backyard Burn at Lake Fairfax in Reston on Oct 19, 2025. Choose a 5.1 mile lap or 10 mile option on mostly singletrack with roots, rocks and rolling climbs while supporting local nonprofit Homestretch.

Event Greensprings 24 is a 24-hour endurance race on Saturday, October 25, 2025, in Williamsburg, VA (3751 John Tyler Hwy). The event benefits The Arc in Williamsburg, VA. Awards are given for completing 50k, 50 miles, 100k, 75 miles, and 1..

Run the scenic, historic trails of Patapsco Valley State Park at the Patapsco Valley 50K, offering 50k and 25k distances plus virtual options. Enjoy well stocked aid stations, commemorative shirts and unique finisher awards.

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 tr..

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 sett..

North Point Fright Night 5K & Haunted Trail is a Halloween-themed community event at North Point High School in Waldorf, Maryland, on October 25, 2025. The day features a 5K on the school’s official cross-country course (certified for compe..

Event overview The Indian Fields Tavern/5 Fields Brewing Co. Low Key Halloween Haunts takes place on Sunday, October 26, 2025, in Charles City, Virginia. The event offers two distances: 5k 10k The published entry fee is $20. The entry inc..

Event The Halloween Horror event on October 26 takes place at Conway Robinson State Forest in Gainesville, VA. Distances offered: 5k 10k Walkers are welcome. A virtual race option is available. Points from the event count toward the 5k, 1..

Event overview The Fall Backyard Burn Trail Run - Riverbend is scheduled for Sunday, November 2, 2025, at Riverbend Park in Great Falls, VA (8700 Potomac Hills Street, Great Falls, VA 22066). The event is produced by EX2 Adventures. Two cou..

Honor Veterans Day on scenic single track at Rosaryville State Park with Annapolis Striders, choosing 50K or 20K looped courses. Limited to 250 runners, this friendly trail race offers rolling climbs, aid stations, and awards.

Tackle the scenic MCRRC Stone Mill 50 mile trail run through forested single track on the Seneca Greenway and Muddy Branch in Montgomery Village. Enjoy rolling terrain, stream crossings and community spirit on November 8, 2025.

Event The Schaeffer Half Marathon, 10K, 5K Trail Run is held on Saturday, November 8, 2025 at Button Farm Living History Center in Germantown, MD. The event is produced by EX2 Adventures and includes in-person races and virtual options for..

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..

Run through Hemlock Overlook's wooded trails and riverside views at the Fall Backyard Burn, with 5 and 10 mile options that highlight rocks, roots and local wildlife. Expect challenging terrain, spectator friendly spots and a community vibe..