Trail Running calendar near Woodstock 2025-2026

Celebrate the season at the Tinsel Trot, a festive 5k and 10k at Southern Revere Cellars in Louisa. Enjoy a chip timed race, technical shirt and a post run glass of wine or beer, with a virtual option and proceeds supporting Serenity Farm.

Join Dash through the Hills on Dec 13, 2025 at Hardware Hills Vineyard for a scenic charity trail 5K or 1.1 mile walk benefiting Caring for Creatures animal sanctuary. Finish at the tasting room with live music, a food truck and wine for pa..

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.

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.

Run the Burke Creek Barn Burner in Palmyra, VA on January 10, 2026 with 5K and 15K trail options in its second year. Enjoy hot drinks, finish line treats with gluten free and vegan choices, and post race awards.

Run scenic trails at Leesylvania State Park on January 17, 2026 and support Food for Others with 5k and 10k distances. Enjoy a mixed trail and pavement course, in person or virtually, with finisher medal and tech shirt for early registrants..

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.

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..

Join the 18th annual ICY 8 at scenic Lake Anna State Park on Feb 7 for 8 hour adventure trail runs, a Half Marathon Plus in a figure 8 format, or a challenging 8 miler. Mostly single and double track trails promise a fun, rugged day outdoor..

Test your limits on this timed trail ultra at Little Bennett Campground with 5 and 9 hour solo and relay options on a scenic 4.4 mile loop. Enjoy aid stations, Altra demos and a post race chili while supporting Montgomery Parks Foundation.

Run through scenic trails at Walnut Creek Park in North Garden with your choice of a 5k or 10 mile trail race, both featuring wooded single track and lake views. Enjoy race swag and post race refreshments at this rain or shine event.

Run a hilly trail 5k or 10k at Wilderness Run in Spotsylvania VA on Feb 14, 2026 and support Semper Fi and America's Fund. Chip timing, finisher medal, tech shirt and a post race beer or wine; virtual option available.

Take on scenic river trails at the Paradise Springs 5k and 10k in Clifton VA on February 28, 2026, featuring challenging rocky sections and plenty of elevation. Finish at Paradise Springs Winery with a finisher medal, tech shirt and a compl..

No Man's 50K is a women only trail running challenge in Triangle, VA with 50K and 25K on scenic single track and forest roads. Two loop courses, full aid stations, and a welcoming vibe make this a must for endurance runners.

Take on scenic forest trails at Conway Robinson State Forest with a 5k or two lap 10k, suitable for runners and walkers of all levels. Support the Lost Dog & Cat Rescue Foundation and earn a finisher coin plus a tech shirt.

Join the scenic Seneca Creek Greenway Trail in Gaithersburg MD on March 7, 2026 for a marathon or an extended 50K. Run single track parkland trails and choose to finish at the marathon or keep going to complete the 50K.

Hit the Blue Ridge trails at Bel Monte Endurance Races in Lyndhurst, Virginia on March 14 with 50 mile, 50K and 25K options across mostly single track trails and mountain roads. Expect big climbs, rugged forest terrain and sweeping views.

Run a scenic 4k or 8k on the rolling grounds of Twisted Oak Farm Brewery in White Post, VA. Enjoy chip timing, a finisher medal, a tech shirt and a complimentary glass of beer, with a virtual option available.

Tackle a 41 mile trail ultra in the Shenandoah Valley with about 8,000 feet of climbing, waterfalls and dramatic cliff overlooks. Limited to 125 runners, this remote loop offers aid stations and a 13 hour 15 minute cutoff.

Run the Bull Run Run 50 Miler on April 4, 2026 in Clifton Virginia, a 50 mile trail through rolling forest and spring bluebells along the Bull Run Occoquan Trail. Civil War themed course, riverside views and a 13 hour cutoff.