Leonardtown
Trail Running Calendar near Leonardtown 2026-2027
Explore the top trail runs near Leonardtown for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Muddy Dash Mechanicsville on Aug 29, 2026 is a family-friendly 5K mud run with obstacles, mud pits, a pre-party and an after-party at Budds Creek Motocross Park.
September 2026
Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.
Sip and Stride 5K is a chip timed run and walk through Running Hare Vineyard in Prince Frederick, Maryland on September 19, 2026. Entry includes a shirt option, a drink ticket for 21 plus, and a finisher medal.
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 on the 300+ acre Running Hare Vineyard in Prince Frederick, MD, featuring a complimentary drink for those 21 and over, live music, finisher medals, apparel options, and proceeds supporting Habitat for Humanity.
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.
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.