Trail Running calendar near Winchester 2026-2027

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.

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..

Barrel Oak 3k & 6k at Barrel Oak Winery in Delaplane VA on April 19, 2026 offers on-site 3 km and 6 km courses plus virtual entries with medal and shirt options; walkers and leashed pets are welcome.

Experience a trail run through Lake Fairfax Park in Reston featuring scenic lake views and smooth singletrack paths. Choose between 5.3 and 10.3 mile distances on a course with frequent short hills and minimal pavement.

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 5K obstacle course at Lubber Run Community Center in Arlington, VA with two loops on the Lubber Run Nature Trail and 1,158 feet of elevation gain. ASC members attend free, non-members pay $50.

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.

Trail races at Camp Harmony around Quemahoning Reservoir include a 50K solo, a four person relay, a 30K lap and a new 10K loop. The forested course features singletrack, rolling hills, aid stations, and a 10 hour cutoff.

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.

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 10K at Fountainhead Regional Park near Washington D.C. Courses feature singletrack with rocks and roots, stream crossings, multiple aid stations, and notable climbs, with chip timing and postrace support.

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.