Trail Running calendar near Leonardtown 2025-2026

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walke..

Run an untimed 14 mile point to point on the scenic Dahlgren Railroad Heritage Trail in King George, Virginia. Enjoy quirky aid station treats and help support local charities through Sheetz For the Kidz.

Run through rows of trees at Ruppert Nurseries in the Breeze Thru The Trees 5K, a scenic cross country course on a 500 acre tree farm. Enjoy a family friendly 1 mile while supporting the Montgomery County Children’s Opportunity Alliance.

Scenic loop racing at Piney Run Park on April 18, 2026 offers 50K, 25K, 5 mile and an 8 hour challenge on woods and meadow trails with lake views. Enjoy aid stations, finisher medals, and charitable support while racing rain or shine.

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no..

Run the Rock Leesburg is a unique trail 5K inside an active rock quarry at Luck Stone, with gravel terrain and scenic views. Family fun, finisher medals and proceeds support the Reeves Community Center Foundation.

Run scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.

Hit the scenic Dash Through the Dirt on the C&O Canal towpath with 5k, 10k and half marathon on light gravel trails. Chip timing, finisher coin and tech shirt included while supporting the EOD Warrior Foundation; virtual option.

Run the Motion for Justice 5k in Rocketts Landing along the scenic Virginia Capital Trail with James River views. Enjoy a finisher medal and technical shirt or go virtual if you cannot attend in person.

Join the Taskinas Creek Hike a Half on June 7, 2026 at York River State Park for an inclusive, no frills trail half that prioritizes fun over speed. Limited to 250 runners, scenic single track and a tough final two miles make for a memorabl..

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, honoring the park's OSS legacy. Choose 50 mile or 25 mile on a scenic single track loop with aid stations and true night race atmosphere.

Hit the scenic B&A Trail in Severna Park for a marathon or half marathon on March 29, 2026. Enjoy wooded waterfront trails and a lively finish at Severna Park High School hosted by the Annapolis Striders.

Take on the rugged MD Heat Trail Race in Elkridge with 25K and 50K options across rolling single track, technical rocky sections, river crossings and more than 2000 ft of vertical gain. Unwind at the post race party with craft beer, real fo..

Explore scenic new hiking trails at Pocahontas State Park with options of a half marathon or 10k, both starting and finishing on the park's grass field. Pro chip timing and live results add a competitive edge to this fall trail run.

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..