Leesburg
Trail Running Calendar near Leesburg 2026-2027
Explore the top trail runs near Leesburg for 2026-2027! We've gathered 58 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Scenic 5 km and 10 km at Burke Lake Park on September 20 with chip timing, tech shirt, medal, virtual option, and proceeds benefiting Operation Turbo.
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 5K, 10K and half marathon at Burke Lake Park on October 3 with chip timing, finisher medal, water stations and a virtual race option.
A chip timed 5k trail race at Claude Moore Park on October 3 with a medal, cotton shirt, virtual option, and series points for multiple season standings.
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 at Conway Robinson State Forest with chip timing, a virtual option, water stations, age awards, and support for Dulles South Soup Kitchen.
A scenic 5K at Rocklands Farm Winery with chip timing, on-course aid, awards, post race wine offerings, live music, and race day amenities.
Scenic 5 km and 10 km trail races at Burke Lake Park with in-person and virtual options supporting The Brain Foundation.
November 2026
Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.
Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.
A chip timed 5k and 10k at Burke Lake Park on November 7, 2026, with trail and paved sections, finisher medal, technical shirt, and a virtual race option.
Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.
A community fundraiser with a timed 5K, a 1.6K nature walk and a 500 m kids run supporting Toca Juniors Football Club and its Smiles Soccer Program.
A 5K and a 1 mile kids fun run at Clarke County Parks and Rec in Berryville on November 14, featuring trail and roadway courses, awards, chip timing and a food drive.