Leesburg
Trail Running Calendar near Leesburg 2026-2027
Explore the top trail runs near Leesburg for 2026-2027! We've gathered 63 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail-based 5k, 10k and half marathon at Burke Lake Park with chip timing, a virtual option, series points, and proceeds benefiting We Rock Cancer.
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 Saree Run at Oatlands Historic House and Gardens in Leesburg on October 4, 2026 raising breast cancer awareness on a mostly grass, rolling course with wooded trails.
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, finisher medal, water stations, a virtual option, and series points.
Scenic 5K through vineyards and farm at Rocklands Farm Winery with chip timing, post run wine options, live music, and awards for overall and age group finishers.
A scenic 5k and 10k at Burke Lake Park with in person and virtual options, chip timing, race day packet pickup, and fundraising for 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.
Chip timed trail and paved races at Burke Lake Park offering 5k and 10k distances, a virtual option, medals and technical shirts.
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 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.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A November event in Brunswick MD with a full marathon, half marathon, and a Veterans Challenge 5K that features towpath running, river crossings, and historic town sections.