Trail Running calendar near Hillsboro 2026-2027

Nighttime training run of 25.9 miles on the Massanutten Mountain Trail that mirrors miles 70 to 96 of the MMT 100. Prior daytime experience on the course is required and one personal aid stop is likely near 15.2 miles.

Experience the rugged terrain of Michaux State Forest with trail races and a half marathon. Navigate creek crossings and forest climbs at Pine Grove Furnace State Park or participate virtually from any location.

Experience a scenic trail run at Pohick Bay Regional Park featuring waterfront views and historic surroundings. Choose between 5.9 and 10.4 mile courses through single track trails with professional support and activities for the whole fami..

Experience a fast and flat race along the scenic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners are invited to set new personal records at Carderock Park.

A memorial trail event at Piney Run Park featuring a 5.25 mile loop used for 50K, 25K, a 5 miler and an 8 hour challenge. Aid stations and loop transition support are provided and finishers receive a hat or visor and a medal.

Enjoy a cross country style 5k run or walk through the scenic Hauser Hill Event Center. Participants receive a finisher medal and a pour of wine in a collectible glass at the finish line.

A trail ultramarathon in Gunpowder State Park with 25K and 50K options on a 15.5 mile loop. Staffed aid stations and a nine hour time limit support runners throughout the course.

Experience the scenic grounds of Barrel Oak Winery in Delaplane, Virginia, through 3k and 6k race options. This inclusive event welcomes both walkers and leashed pets for a day of activity in a beautiful vineyard setting.

Trail run at Lake Fairfax Park in Reston, VA featuring mostly smooth singletrack, lake views, and short technical sections. Choose 5.1 miles (one lap) or 10 miles (two laps) with options for swag, optional medals, and a supervised kids prog..

Experience a scenic 5K cross country race through the hop yards and vineyards of Red Shedman Brewery. Finishers enjoy a complimentary beverage at this unique farmhouse event in Mount Airy.

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 scenic trails of Third Winchester Battlefield Park with 5k, 10k, and half marathon distances. This historic Virginia event welcomes both runners and walkers for a beautiful spring race.

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.

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.

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.

Join the inaugural Run Rock Creek 5K/10K in Washington D.C. to experience a forest run through America’s premier urban national park while supporting vital trail restoration and conservation efforts.

Participate in a scenic trail run in Lorton to support Gunston Elementary School. This community event features 10K, 5K, and Fun Run distances with proceeds funding student enrichment and arts programs.