Trail Running calendar near Hillsboro 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.

A spring race at Third Winchester Battlefield Park on April 25 2026 offering 5K 10K and a Half Marathon, with walkers welcome and virtual entry options that include medal or shirt packages.

Experience a unique trail race through an active rock quarry at the Luck Stone Leesburg Plant. This 5K event supports environmental preservation and features family activities and awards for all ages.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

Run a scenic 5k around the Bluemont Station Brewery property in Virginia. The event welcomes both runners and walkers and offers in-person and virtual participation options.

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.

Trail event at Agricultural History Farm Park in Derwood, Maryland offering marathon, 25K and timed 3 hour, 6 hour and 10 hour challenges on five mile laps with on course aid options.

The Perfect Day 50K takes place on the Massanutten Western Slope in Keezletown, Virginia. Runners can compete individually or as part of a two or three person team on a Saturday in May. The event offers a full day on the trails.

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.

A trail run on May 2, 2026 at 10709 Gunston Rd in Lorton offering a Fun Run, 5K, 10K and virtual options. Proceeds support no-cost enrichment programs at Gunston Elementary School.

Trail half marathon and an about 11K course at Fountainhead Regional Park near Washington DC, featuring rocky, rooty singletrack, stream crossings, notable elevation, and multiple aid stations with water and Gatorade.

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.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

A multi distance trail event in Waterford VA on May 9, 2026 that runs through historic village streets, vineyards, trails and unpaved roads. Proceeds support the Waterford Foundation and 5K and 10K finishers receive a shirt and medal.

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.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

A 100 mile trail ultramarathon in the Massanutten Mountains near Fort Valley, VA, run on rocky trails with over 18,000 feet of ascent and a 36 hour cutoff. Start and finish are at Caroline Furnace Lutheran Camp; entry is open.

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.