Trail Running calendar near Germantown 2025-2026

Tackle the Massanutten Mountain Trails 100, a 100 mile ultramarathon in Virginia's Shenandoah Valley with over 18,000 feet of climbing on rocky, rugged trails. You get 36 hours, live volunteer timing, well stocked aid and required GPS track..

Run the Dash Through the Dirt May 16, 2026 at Carderock on the scenic C&O Canal towpath in Potomac MD. Choose 5k, 10k or half marathon on light gravel with chip timing, tech shirt and finisher coin. Proceeds benefit EOD Warrior Foundation.

Run the Conestoga Crusher on May 16, 2026 at Kelly's Run in Holtwood PA with 10K, 5K and a kids 1.5 mile trail run. Tackle creek crossings, climbs and the Pinnacle Overlook on scenic trails while supporting the Lancaster Conservancy.

Join the Night Raider at the Winery at Bull Run on May 22, 2026 for a festive evening 5k or 10k through scenic Manassas Battlefield trails. Enjoy chip timed results, a finisher medal, a technical shirt and a complimentary glass of wine.

The Old Dominion is a 100 mile loop through the Massanutten Mountains, offering rugged climbs and mixed road and trail terrain. Part of the Grand Slam of Ultrarunning, it runs June 6, 2026 with a 24 hour silver buckle cutoff.

Run a flat, fast five mile out and back along the shaded C&O Canal Towpath in Williamsport, MD on June 6, 2026. Enjoy chip timing, tech shirt options and age group awards in a friendly community race.

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, with 50 mile, 25 mile and 10 mile options on scenic single track and fire roads. Expect rugged trails, moonlit views and well stocked aid stations.

Take on the Sweet Air Trail Race at Gunpowder State Park on July 12, 2026, a scenic out and back with rolling hills, faster stretches, water crossings and a bit of mud. Limited to 100 runners, entry is free and donations are welcome.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run through rolling vines at 868 Estate Vineyards in Hillsboro with a scenic but hilly 5k or 10k course that tests and rewards. Finishers get a medal, tech shirt and a glass of vineyard wine, and a virtual option is available.

Run the scenic Third Winchester Battlefield on Aug 8, 2026 with 5k, 10k or half marathon options on mostly gravel trail. Chip timed event with finisher medal, tech shirt and virtual option, supporting Operation Enduring Warrior.

Take on the MD Heat Trail Race in Patapsco Pickall near Elkridge with 25K and 50K options on rolling, technical single track with river crossings and rewarding climbs. Relax at the finish with food, beer and a festive post race vibe.

Enjoy a scenic trail 5k or 10k through Leopold's Preserve in Broad Run, Virginia on Aug 23, 2026, with chip timing, medals and a tech shirt. Walkers and virtual participants are welcome and races earn points toward year long series.

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.

Join the Sasquatch Preservation Trail Run in scenic Seven Valleys, PA on September 12, 2026 for a fun 5K or 10K through rolling trails and forest scenery. Volunteers welcome to help keep this community event running strong.

Run to the Taproom at Creekside Farm Brewery in King George offers 5K and 8K trail runs through a scenic farm along the Rappahannock River. Finish with live music, food trucks and a complimentary beer for participants 21 and over.

Trails 4 Tails at Codorus State Park offers a scenic, rolling course for the 40 mile ultra, team relay or 25K with mixed singletrack, fields and lake views. Full aid station, camping and nearby lodging make it a fun day on the trails.

Join the Howlin' Coyote Canicross Trail Race in King George VA for a scenic, dog friendly trail run that benefits Friends of Caledon State Park. Enjoy varied terrain, reusable speedCups and the chance to race with your leashed pup.

Join the Kettle Cooker Five & Dime at Glenroy Preserve for scenic loop trails with 5 mile, 10 mile and 25K options over hills, creeks and rocky terrain. Chip timing, aid stations, a soft tee and post race beer make it a great day.

Run scenic, historic trails in Patapsco Valley State Park with 50k and 25k options plus virtual entries that include same shirt and award. Enjoy well stocked aid stations, volunteer support, and a festive finish near CCBC Catonsville.