Leonardtown
Trail Running Calendar near Leonardtown 2026-2027
Explore the top trail runs near Leonardtown for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.
A scenic chip timed 5K at Running Hare Vineyard on October 11, 2026 with a complimentary drink for those 21 plus and post-race music and photos.
November 2026
Trail and virtual runs at Valor Ranch in King George VA featuring timed 10K and 5K events, a 10K ruck, a 1 mile fun run, and 100 percent of proceeds supporting Valor Ranch charitable programs.
January 2027
Experience a scenic out and back half marathon on the flat and smooth Dahlgren Railroad Heritage Trail. Enjoy a unique post race campfire with roasted donuts and earn a custom finisher medal.
February 2027
Loop trail races at Saint Marys Lake near Leonardtown, MD offering 17K, 34K, and 50K options with marked trails, aid stations, and on-course support.
March 2027
St. Paddy's Day 5K and 1 mile walk at Creekside Farm Brewery with a scenic trail, chip timing, awards, music and Irish activities.
April 2027
A 14 mile untimed point to point trail run along the Dahlgren Railroad Heritage Trail that starts at one Sheetz and finishes at another. The event features unusual aid station snacks and practical finisher swag.
Runs through 50 acres of vineyards at Ingleside Vineyards with 5K and 8K chip timed courses, plus post race wine and live music.
5K run and 1.5 mile walk at Corteau Vineyards in Mechanicsville, MD on April 11, 2027, timed and scored by J3 Timing.