Trail Running calendar near Winchester 2025-2026

Run a scenic fall trail through Manassas National Battlefield from The Winery at Bull Run with 5k and 10k options, in person or virtual. Enjoy a postrace glass of wine and a finisher medal while supporting the Manassas Battlefield Trust.

Celebrate Thanksgiving at the 21st Annual Catonsville High School XC Turkey Trot with a cross country style 5K and 1 Mile Family Fun Run in Catonsville, Maryland. Proceeds support the CHS cross country program.

Celebrate Thanksgiving at the Lake Anna Turkey Trot on November 28, 2025 at Lake Anna State Park. Run a 5k, 10k or half marathon on scenic trail and road courses with a tech shirt, finisher medal and chip timing, or join virtually.

Join the Giveback Community 5K on Saturday November 29, 2025 in Derwood MD for a friendly run or walk at Needwood Trail. Skip the entry fee and bring two nonperishable food items to support the Give Back Initiative and local families.

Devil Dog Ultras in Prince William Forest Park offers 50K, 100K and 100 mile trail loops on well marked single track and rolling fire roads. Expect staffed aid stations, limited bunkhouse beds and a lively winter ultrarunning weekend.

Tackle scenic trails around Occoquan Reservoir at the Fall Backyard Burn Trail Run in Fountainhead Regional Park on Dec 7, 2025. Choose a 4.8 or 10.5 mile route, enjoy course support and post race food while supporting Homestretch.

Enjoy a scenic 13.1 mile run along the C&O Canal Towpath at the Founders Half Marathon in Potomac, part of the DCRR Snowball Series. Friendly on course support and post race snacks make this a welcoming community event.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

Celebrate the season at the Holiday 4 Miler in mid December at Lake Accotink Park in Springfield. Run a scenic loop on paved and dirt trails along the CCT, with in person and virtual options.

Join the Food for Others 5k and 10k at Leesylvania State Park on Jan 17, 2026 for scenic trail and paved sections, small hills, and a festive finish with tech shirts and medals. Proceeds benefit the charity and a virtual option is available..

Run the Mid Maryland Trail Festival at Rockburn Branch Park in Elkridge, MD, a scenic 50K on wooded trails made up of six loops of about 5.18 miles each. Solo runners or teams up to six can tackle the full distance or share loops in a relay..

Run the Patriotic Pursuit in Williamsport Park with 5k, 10k and half marathon options along the scenic flat C&O Canal Trail by the river. Chip timing, tech shirts, finisher medals and a virtual option support Semper Fi & America's Fund.

Enjoy a scenic trail run along the Little and Middle Patuxent rivers in Columbia, Maryland. Choose from a half marathon, 10K or 5K on Jan 31 to Feb 1, 2026 at the Guilford Pratt Truss Bridge for a tame and rewarding trail experience.

Brave wooded trails at Prince William Forest Park on Feb 1, 2026 with distances from 5k to 50k, featuring technical hills, roots and scenic views. Support Semper K9 and earn medals, tech shirts and chip timing in this winter trail challenge..

Challenge the figure 8 trails at Lake Anna State Park in the 18th annual ICY 8, featuring an 8 hour adventure trail run and a Half Marathon+ on a looped course. Runners and hikers are welcome with scenic single and double track and generous..

Run a timed trail ultra at Little Bennett Campground on scenic 4.4 mile loops, choosing 5 or 9 hour solo or relay challenges. Enjoy aid stations, Altra shoe demos, a long sleeve race top and a post race chili bar while supporting Montgomery..

Hit the scenic hilly 5k or 10k across historic Chancellorsville and Wilderness battlefields on February 14, 2026. Walkers welcome, proceeds benefit Semper Fi and America's Fund, and finishers enjoy a beer or wine plus a commemorative medal.

Take on a technical trail at Paradise Springs with rocky riverside singletrack in 5k or 10k. Finishers get a medal, technical shirt and a glass of wine while supporting the John P. Mayhugh Foundation.

Join the Bigfoot Endurance 5 and 10 Mile at Rockburn Branch Park on March 1 2026, with a team relay option. Get a long sleeve shirt, finisher medal and two post race beers while supporting Parkinson's research on scenic gravel and natural t..

No Man's 50K is a women only trail race in Triangle, VA offering 50K and 25K across two scenic 15 mile loops. Limited to 120 entrants, the course is mostly single track with stocked aid stations.