Trail Running calendar near Leonardtown 2024-2025

We have found 45 Trailruns within 80 miles of Leonardtown. See below where and when you can find the races.

The Tuckahoe 25K is an exciting trail running event scheduled for November 23, 2024, in Queen Anne, MD. This race, organized by the Centreville Crushers and Algonquin Ultras Inc., offers a challenging yet accessible 25K course that features a mix of single-track and wider horse trails. Participants ..

The Fall Backyard Burn Trail Run at Fountainhead Regional Park offers an exciting opportunity for runners to enjoy the beautiful trails along the Occoquan Reservoir. Scheduled for November 24, 2024, participants can choose between a 5-mile or a 10-mile course, both featuring scenic hiking trails and..

The Winery at Bull Run Turkey Trot features a scenic 5k and 10k run through the historic Manassas National Battlefield, taking place on November 27. This event is part of the Sippin Series and offers a virtual race option for participants unable to attend in person. Runners will receive a glass of w..

The 20th Annual Catonsville High School XC Turkey Trot is a cherished community event celebrating health and wellness. Scheduled for November 28, 2024, it features a 1 Mile Family Fun Run and a 5K race, both of which are timed. The event is designed to foster community spirit, with all proceeds bene..

The Drumstick Dash 8 Miler is a festive running event held on Thanksgiving Day, inviting participants to celebrate the holiday with a fun run. The event features a scenic, flat out-and-back course along the Mount Vernon Trail, extending to Teddy Roosevelt Island. Runners can enjoy a chip-timed race,..

The 26th Milford Cross Country Booster Reindeer Stampede 5k is set to take place at Killens Pond State Park in Felton, Delaware, on November 30, 2024. This annual event supports the Milford High School Cross Country team and features a scenic 5k run/walk. Participants can pre-register for a fee, wit..

December 2024

The Winter Tour in Salisbury, MD, is an exciting running event that takes place over December and January, featuring eight unique routes across Delmarva. Participants can run or walk at their own pace, with the option to compete for podium spots using Strava for verification. Runners can complete th..

The Winter Lake Anna Half event features a scenic and challenging course at Lake Anna State Park, offering participants the choice of a 5k, 10k, or half marathon. The 5k is a trail run, while the 10k and half marathon consist of a mix of trail and paved road. Walkers are welcome, and there is a time..

Devil Dog Ultras is a trail running event held in Prince William Forest Park, Virginia, featuring 100-mile, 100K, and 50K races. The course consists of primarily single-track trails with some technical sections, fire roads, and rolling hills. Runners will complete loops of varying lengths, with well..

The Fall Backyard Burn Trail Run at Hemlock Overlook is a scenic trail running event scheduled for December 8, 2024, in Clifton, Virginia. Participants can choose between two distances: a 5-mile or a 10-mile course, both featuring a mix of forested fire roads, hiking trails, and open fields. The rac..

The Santa’s Summit 7.5 Miler is a scenic trail running event taking place at Bull Run Marina, featuring a challenging course along the Bull Run Occoquan Trail. Participants can choose between a 7.5-mile and a 7k distance, with both races contributing points towards year-long running series. Runners ..

The Tinsel Trot 10k, held in Louisa, VA, is a festive running event that takes place at Southern Revere Cellars. Participants can choose between a 10k and a 5k race, both of which contribute points to various running series. Runners receive a technical event shirt and a complimentary glass of wine o..

The Pocahontas Half, along with a 10k and 5k, is a scenic running event taking place at Pocahontas State Park near Richmond. Participants can enjoy a beautiful forest trail run featuring a mix of dirt and pine needles, with varying elevations. The event welcomes walkers and strollers, and offers a v..

January 2025

The Mid-Maryland Trail Festival features a 50K race and a 50K relay, taking place on a scenic wooded trail in Elkridge, MD. Participants will complete six loops of approximately 5.179 miles each, with options for solo runners or relay teams of up to six members. The event offers various distance opt..

The Leesylvania 10k is a trail running event taking place at Leesylvania State Park, featuring a scenic course that includes both trails and pavement, with some small hills and a staircase. Participants can also opt for a virtual race option. Runners receive a finisher’s medal, a technical event shi..

The Snowy Owl 10 Mile is a trail race set in the scenic York River State Park in Williamsburg, VA. Scheduled for January 5, 2025, the course features a mix of technical single track and dirt fire road trails, with an elevation gain of approximately 600 feet. Participants can expect rocky sections, t..

The Winter Conway Robinson 10k is a trail running event taking place at Conway Robinson State Forest Park. Participants can enjoy a scenic loop route featuring technical terrain and minor hills. The event includes both a 10k and a 5k option, with points contributing to various series standings.Runne..

The Angela Ivory Memorial Runs take place at Killen's Pond State Park in Felton, DE, featuring a 100-mile, 50K, and 24-hour race. The course consists of a 3.10-mile dirt loop with minimal technical challenges, making it accessible for various runners. This event is self-supported, encouraging partic..

February 2025

The ICY-8 event in Spotsylvania, VA, is an exciting trail running experience that features an 8-hour adventure trail run and a new HALF MARATHON+ option. Set in the scenic Lake Anna State Park, participants can choose from various loop courses, including 8.0 miles, 4.7 miles, and a mini loop of 1.5 ..

The Great Frosty Forest Marathon, taking place on February 2, 2025, features a 5k, 10k, and half marathon through the scenic trails of Prince William Forest Park. This event supports a charitable cause and welcomes both runners and walkers. Participants will receive a finisher's coin, a technical ev..