Hillsboro
Trail Running Calendar near Hillsboro 2026-2027
Explore the top trail runs near Hillsboro for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.
Trail 5k and 10k at Conway Robinson State Forest with chip timing, finisher medal, water stations, a virtual option, and series points.
A scenic 5K at Rocklands Farm Winery with chip timing, on-course aid, awards, post race wine offerings, live music, and race day amenities.
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 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.
A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are requested.
Half marathon, 10K and 5K on the C&O Canal towpath from Great Falls Tavern on Nov 21, 2026 with live tracking, a capped field, and scratch made donuts and pizza at the finish.
Trail race at Riverbend Regional Park near the Potomac offering 5 mile and 10 mile loop options with riverside singletrack, aid stations, and post race food.