Trail Running calendar near Frederick 2025-2026

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.

Conestoga Crusher invites trail runners to tackle scenic 10K and 5K courses plus a free kids race at Kelly's Run Nature Preserve. Expect creek crossings, big climbs and a Pinnacle Overlook with Susquehanna River views while supporting Lanca..

Tackle the legendary Old Dominion 100, a 100 mile cross country endurance run near Fort Valley, Virginia with a history dating to 1979. Expect rugged mixed terrain, volunteer support and a silver buckle for finishes under 24 hour.

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..

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.

Sprint or stroll through scenic countryside at the Sasquatch Preservation Trail Run 5K and 10K in Seven Valleys, Pennsylvania on September 12, 2026. Celebrate the 15th running with trails for every level and watch for registration details.

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..