Trail Running calendar near Leonardtown 2025-2026

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..

Get spooky on October 26 with the Halloween Horror trail run at Conway Robinson State Forest in Gainesville, VA. Choose 5k or 10k in person or virtual and enjoy a technical event shirt and finisher medal for all finishers.

Join the 4th annual Trailblazer Trot 5K and Monster Mile at CTEC to support scholarships for local students. Costumes are welcome for this festive Halloween fun run, and awards follow the 5K.

Join EX2 Adventures on Sunday November 2 at Riverbend Park for a scenic Fall Backyard Burn along Potomac riverside singletrack. Choose a 5 mile lap or a 10 mile double lap on runnable trails with a few short climbs and a post race vibe.

Take on 50 miles of scenic single track through the Seneca Greenway and Muddy Branch trails in Montgomery Village, Maryland on November 8, 2025. Expect rolling forest terrain, stream crossings and a rewarding day on the trails.

Run the 16th annual Rosaryville Veterans Day Trail Race at Rosaryville State Park with 50K and 20K routes through woods and meadows on rolling single track trails. Limited to 250 runners with aid stations and awards.

Enjoy fall trail racing at Button Farm Living History Center in Germantown, MD with a half marathon, 10K, 5K and a free kids race benefiting Interfaith Works. Expect twisty singletrack, open farm field views, medals, post race food and awar..

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..

Join the Fall Backyard Burn at Hemlock Overlook for scenic trail running along Bull Run with roots, rocks and stream crossings. Choose 5.2 or 9.5 miles and enjoy aid stations, race swag and a lively finish.

Event details The 2025 Herndon Turkey Trot is a cross-country style 5K held on November 22 at the Herndon Community Center, 814 Ferndale Ave., Herndon, VA. The race is open to participants age 4 and up. Runners must complete the 5K in 45 mi..

Tuckahoe 25k in Queen Anne Maryland is a scenic trail run with runnable hills and rooty, muddy sections. Three aid stations and event swag await finishers on Saturday, November 22 for a fun, rugged autumn challenge.

Join the Freeze Your Gizzard 5K or 1 Mile on Nov 22 at Ida Lee Park in Leesburg for a scenic but challenging cross country course and lively community vibe. Pre registered 5K runners receive a long sleeve shirt and the event supports Loudou..

Run forest and meadow singletrack at the Fall Backyard Burn Trail Run at Laurel Hill, staged from the historic Workhouse Arts Center in Lorton VA. Choose one 5.4 mile lap or two laps for 10 miles and enjoy aid stations and post race food.

Run a scenic fall trail through Manassas National Battlefield from The Winery at Bull Run with 5k and 10k options, in person or virtual. Enjoy a postrace glass of wine and a finisher medal while supporting the Manassas Battlefield Trust.

Join the 21st Annual Catonsville High School Turkey Trot on Thanksgiving morning for a family friendly 1 Mile fun run and a competitive chip timed 5K in Catonsville, Maryland. All proceeds support the CHS cross country program.

Celebrate Thanksgiving at the Lake Anna Turkey Trot on November 28, 2025 at Lake Anna State Park. Run a 5k, 10k or half marathon on scenic trail and road courses with a tech shirt, finisher medal and chip timing, or join virtually.

Join the festive 27th Milford Reindeer Stampede at Killens Pond State Park on November 29, 2025 for a chip timed 5K run or competitive walkers only 5K. Enjoy a long sleeve tee and a cozy post race party with treats and photos.

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 tr..

Devil Dog Ultras in Prince William Forest Park offers 50K, 100K and 100 mile trail loops on well marked single track and rolling fire roads. Expect staffed aid stations, limited bunkhouse beds and a lively winter ultrarunning weekend.

Join the Fall Backyard Burn at Fountainhead Regional Park for scenic trail running around the Occoquan Reservoir with shorter and longer course options. Post race food, music and charity support add to the fun.