Trail Running calendar near Frederick 2025-2026

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.

Run through vineyards at Barrel Oak Winery on 3k and 6k cross country courses with gravel and rolling hills. Enjoy a finisher medal, tech shirt and a glass of wine while supporting Semper Fi and America's Fund, virtual option available.

The C&O Canal 100 is a scenic 100 mile ultramarathon along the Potomac on the C&O Canal towpath, starting and finishing at Camp Manidokan on April 25, 2026. Expect smooth low elevation terrain, reliable aid stations and a Western States qua..

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.

Lace up for the Bluemont Station Brewery and Winery 5k on April 26, 2026, a three lap cross country run around scenic winery grounds with some rolling hills. Walkers are welcome and a virtual option lets you join from anywhere.

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.

Challenge yourself on the Massanutten Mountain Trails 100 Mile Run, a rugged trail ultramarathon in Virginia with more than 18,000 feet of climbing. Expect rocky singletrack, well stocked aid stations, and a 36 hour cutoff.

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.

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This..

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.

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..

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.

Run the Kettle Cooker Five & Dime Trail Race in early October at Glenroy Preserve in Nottingham PA. Choose 5 mile, 10 mile or 25K loops over hilly trails and creek crossings, with chip timing, aid stations, a soft tee and after race food an..

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..