Leonardtown
Trail Running Calendar near Leonardtown 2026-2027
Explore the top trail runs near Leonardtown for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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
Trail running at Saint Marys Lake in Leonardtown, MD offering 17K, 34K and 50K on a roughly 10.5-mile loop with two aid stations and a 100-runner field.
March 2027
A St. Paddy's Day themed 5K and 1 Mile walk at Creekside Farm Brewery in King George, VA, with music, awards, and finisher shirt and pint glass.
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.
A chip timed 5K run/walk at Corteau Vineyards on a two lap grass course through the vines, with race swag, a wine pour and proceeds supporting ZERO Prostate Cancer.
May 2027
A 5 km trail race at Caledon State Park on May 1, 2027, part of the Friends of Caledon Race series and dog friendly with leash rules; fee supports park programs.
A chip timed 5K at Running Hare Vineyards on May 15, 2027 with finisher wine and a stemless glass, race shirts, medals, live music and age group awards.
August 2027
Trail races on the Dahlgren Railroad Heritage Trail in King George VA, with a 50K and a half marathon plus finisher shirts and medals.
Family-friendly mud run with obstacles, mud pits, a pre-party and post-race party at Budds Creek Motocross Park in Mechanicsville on August 28, 2027.