Hillsboro
Trail Running Calendar near Hillsboro 2026-2027
Explore the top trail runs near Hillsboro for 2026-2027! We've gathered 36 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Run or walk 5K, 10K, or a half marathon on scenic routes at Third Winchester Battlefield in Winchester, VA on August 8, 2026.
A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.
September 2026
Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.
The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.
SPEAR 50K is a 50 kilometer trail race on September 19, 2026 at Sherando Park in Stephens City, Virginia. It is part of the Sherando Park Endurance Athletic Runners summer trail series and lists details and registration on RunSignUp and Facebook.
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.
Trail and bike events at Sherando Park on September 26, 2026 offering a 4 mile trail race, a one mile untimed fun run, and a 5.3 mile mountain bike time trial. Proceeds benefit the I'm Just Me Movement.
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
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..
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 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; walkers are welcome.
Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.
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.