Trail Running calendar near Woodstock 2025-2026

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.

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.

Run scenic but technical forest loops at Conway Robinson State Forest on March 7, 2026 with 5k and 10k options plus a virtual race. Support Lost Dog and Cat Rescue and earn a finisher coin, tech shirt and chip timing.

Tackle the MCRRC Seneca Creek Trail Marathon or push on to the 50K in scenic Seneca Creek State Park. Expect hilly muddy rocky single track and a choose your distance finish for a customizable trail challenge.

Join the Smoketown Brewery 5k and 10k on March 8 for flat gravel out and back routes, with a virtual option and walkers welcome. Finishers get a medal, tech shirt, chip timing and a beer while supporting Wear Blue Run to Remember.

Tackle rugged singletrack in the Blue Ridge at Bel Monte Endurance Races on March 14, 2026 in Lyndhurst, Virginia. Pick 50 Mile, 50K or 25K and earn sweeping views and big climbs on classic mountain trails.

Run a scenic cross country course at Twisted Oak Farm Brewery in White Post with 4k and 8k. Enjoy chip timing, a finisher medal, a technical shirt and a free beer, or run virtually if you cannot make it.

Tackle the Hone Quarry Ultra, a rugged 41.4 mile trail through the Shenandoah Valley with about 8,000 feet of climb and stunning cliffs, waterfalls and open meadows. Limited to 125 runners, this remote loop offers big views, six aid station..

Run the Bull Run Run 50 mile trail on April 4, 2026 in Clifton VA, through spring forests, bluebell meadows and Civil War sites along the Occoquan River. Teams, training runs and supportive race amenities welcome all abilities.

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walke..

The Trail Demon 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features a technical forest trail loop with tree roots, rocks, and elevation changes, offering scenic views and a demanding..

Run through rows of trees at Ruppert Nurseries in the Breeze Thru The Trees 5K, a scenic cross country course on a 500 acre tree farm. Enjoy a family friendly 1 mile while supporting the Montgomery County Children’s Opportunity Alliance.

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no..

Mountain & Vine Vineyard 3k, 6k, & 9k takes place at Mountain & Vine Vineyards in Faber, Virginia (500 Delfosse Winery Ln.). The course loops the winery property: 3k is one lap, 6k two laps, and 9k three laps, delivering a hilly but scenic..

Run through vineyards at Barrel Oak Winery on 3k and 6k cross country courses with gravel and rolling hills. Enjoy a finisher medal, tech shirt and a glass of wine while supporting Semper Fi and America's Fund, virtual option available.

The C&O Canal 100 is a scenic 100 mile ultramarathon along the Potomac on the C&O Canal towpath, starting and finishing at Camp Manidokan on April 25, 2026. Expect smooth low elevation terrain, reliable aid stations and a Western States qua..

Run the Rock Leesburg is a unique trail 5K inside an active rock quarry at Luck Stone, with gravel terrain and scenic views. Family fun, finisher medals and proceeds support the Reeves Community Center Foundation.

Lace up for the Bluemont Station Brewery and Winery 5k on April 26, 2026, a three lap cross country run around scenic winery grounds with some rolling hills. Walkers are welcome and a virtual option lets you join from anywhere.