Trail Running Calendar Maryland 2026-2027

A *100-mile* ultramarathon on the C&O Canal towpath near the Potomac River, run as one ~40-mile loop plus two ~30-mile loops. Aid stations appear every 3–6.9 miles and the event is a WSER 2027 qualifier.

Experience the fourth annual trail run at Mount Aetna Adventist School in Hagerstown. Choose between a 3k or 5k course to support student projects and enjoy fitness within a community setting.

Farm Park Challenge is a trail running event at the Agricultural History Farm Park in Derwood, Maryland on May 2, 2026. Options include a marathon, a 25K, and timed three hour six hour and ten hour challenges run as five mile laps.

A timed trail event at the Pocomoke YMCA that runs from sunrise to sunset, where runners complete 3.3 mile laps across mostly single track trail for about 13 hours and 41 minutes. Aid, YMCA facilities, rest areas, and awards are provided.

A community 5K and 10K in Rock Creek Park on May 2, 2026, organized by Rock Creek Conservancy. The event blends trail and road running with guided tours, awards, and activities while supporting park restoration and future improvements.

Join the 10th annual cross country event at Spencerville Adventist Academy featuring a 5K, 1 Mile run, and Kids Fun Run. Enjoy a campus course with finisher medals, team options, and a costume contest for all participants.

A fundraising 5K run/walk through My Lady's Manor in Monkton, Maryland, supporting The Harford Land Trust and The Manor Conservancy. Includes awards by overall and age groups and a post race happy hour with finger foods.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

A trail event at Cromwell Valley Park on May 9, 2026 offering 25k, 12.5k and a family 5k with mostly single track trails and mile marker activities for kids. Proceeds support local conservation groups.

A Mother's Day 5k and 10k in Silver Spring, Maryland, held by Swift Running with a course that passes through Martin Luther King Jr. Recreational Park. The event offers in person and virtual entries with tiered registration fees.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

Experience a fast and flat race along the historic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners of all kinds are welcome at Carderock Park.

Join the Ed Poling Memorial HARC Hike for Hunger & Hope, now in its 14th year. Choose from scenic C&O Canal Towpath hikes in May or a challenging Appalachian Trail hike. This fundraising event supports local community programs.

Test your resilience in this 24 hour endurance challenge in Annapolis. Set your own mileage goals to honor military heroes while enjoying provided meals and a community trail running environment.

A morning 5K held during the Fair Hill Scottish Games on May 16, 2026, with a $40 entry that includes game admission; on-site cash entries and ATMs are available, and cash prizes plus a trophy and Scottish claymore are awarded to top finish..

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

A backyard ultra at Manidokan Camp in Knoxville, MD on May 30, 2026, featuring official 4.167 mile laps and a 1 mile 24 hour event. On-site camping, aid station, showers, timing, shirts, and cash prizes for the winner and the assist.

Join the 14th annual Hike for Hunger & Hope with two events. Choose a challenging 10 or 20-mile Appalachian Trail hike in May or a scenic 5K/10K on the C&O Canal. All hikes support local food programs and refugee services.

Test your endurance at Operation CENTURION on the Rock Creek Trail near Washington D.C. Complete ten 10 mile loops for a total of 100 miles within a 32 hour time limit.