Leesburg
Trail Running Calendar near Leesburg 2026-2027
Explore the top trail runs near Leesburg for 2026-2027! We've gathered 59 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 3 mile cross country race through Nottoway Park in Vienna, VA on 08/30/2026 with a kids dash and a club picnic that includes food and drinks. Registration is free for members and $10 for nonmembers.
September 2026
Fast, flat 5K, 10K and half marathon at Carderock Recreation Area on September 6, 2026, with virtual options and walkers welcome.
A scenic trail event at Burke Lake Park on September 7, 2026, offering in-person 5K and 10K distances plus virtual options; walkers are welcome.
A women only trail event at Fountainhead Regional Park offering a half marathon and a 10k plus on September 12, 2026. Registration runs June 8 to September 1 and two training runs are scheduled in August.
Trail 5K and 10K around Burke Lake in Fairfax Station on September 20, 2026, with in-person and virtual registration options.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
October 2026
Trail courses at Burke Lake Park on October 3, 2026 offering 5K, 10K, half marathon and virtual options; walkers are welcome.
A community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race backpack-pack..
A trail 5K at Claude Moore Park on October 3, 2026, part of the Run Your PRCS Parks timed series, with in-person and several virtual entry options.
A 5K at Oatlands Historic House and Gardens on Oct 4, 2026 supporting Breast Cancer Awareness, with t-shirts, medals, and a mixed grass and trail course.
Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.
A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.
Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.
Trail 5K and 10K races at Conway Robinson State Forest in Gainesville, VA on October 25, 2026, with in-person and virtual entry options.
Scenic 5K at Rocklands Farm Winery featuring cross country style trails, chip timing, age group awards, postrace wine tasting and family friendly amenities.