Annandale
Trail Running Calendar near Annandale 2026-2027
Explore the top trail runs near Annandale for 2026-2027! We've gathered 72 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 races of 5k, 10k and a half marathon at Laurel Hill Park with chip timing, finisher coin, technical shirt, a virtual option, and multiple water stations.
Marathon and half marathon on the C&O Canal Towpath at Fletcher's Cove in Washington DC with a mostly flat Boston qualifying course and age group awards.
A chip-timed charity run at Prince William Forest Park offering 5k, 10k and half marathon distances, trail and pavement courses, and a virtual option.
A trail 5k and 10k at Conway Robinson State Forest with chip timing, finisher medal, technical shirt, water stations, and a virtual option.
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 5k and 10k at Burke Lake Park on mostly paved trails, with a virtual option, chip timing, race shirts and medals, and proceeds supporting The Brain Foundation housing program.
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.
Trail and paved 5 km and 10 km courses at Burke Lake Park with chip timing, medal and shirt, virtual option, water stations, and awards for overall and age categories.
50K and 20K trail races on largely single track loops through Rosaryville State Park near Upper Marlboro, MD, organized by Annapolis Striders.
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.