Trail Running calendar near Little Orleans 2025-2026

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.

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.

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.

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..

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..

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.

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.

Run a flat, out and back 5k or 10k along Brunswick's scenic gravel path and support Wear Blue: Run to Remember. Finishers get a medal, technical shirt and a beer, with virtual options available for out of town runners.

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.

Take on Bull Run Run 50, a 50 mile trail through rolling forest and sweeping bluebell stands along the Occoquan River. This spring ultra mixes scenic singletrack with a local Civil War theme and Trail Sisters approved equal podiums.

Enjoy a scenic three loop 5k through Molon Lave Winery in Warrenton on April 4, 2026. Walkers and virtual runners welcome and finishers receive a winery glass, medal and tech shirt for a festive post race celebration.

Hit the forest trails behind Dirt Farm Brewing for the Trail Demon 5k or 10k with beer, medals and chip timing on April 4, 2026. Run in person or virtually and support Boulder Crest Foundation serving veterans and first responders.

Tackle muddy singletrack, stream crossings and rolling hills at Canoe Creek State Park with your choice of about 10K or a half marathon. Family friendly and charity minded, this spirited trail race welcomes ages 8 to 100.

UltraTrax Wisp at Wisp Resort in McHenry MD on April 11, 2026 invites runners to tackle 7, 14, 21 or 28 mile loops over scenic ridgelines and ski runs with almost 2,000 ft of climbing. Aid, timing, finisher swag and a post race party await.

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.

Scenic loop racing at Piney Run Park on April 18, 2026 offers 50K, 25K, 5 mile and an 8 hour challenge on woods and meadow trails with lake views. Enjoy aid stations, finisher medals, and charitable support while racing rain or shine.

Tackle a scenic, chip timed 5k at Hauser Hill Event Center over cross country trails with rolling hills and uneven footing. Celebrate at the finish with a super soft tee, finisher medal, collapsible wine glass and a pour of wine.

Run 3k or 6k through Barrel Oak Winery vineyards in Delaplane VA on April 19, 2026 for a rolling cross country experience. Enjoy a glass of wine, a medal and tech shirt while supporting Semper Fi and America's Fund; virtual and pet friendly..

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 under the stars at Coopers Rock State Forest on April 25, 2026, choosing a challenging 50 km or half marathon through overlooks, boulders, and steep climbs. Field limited to 250 runners so secure your spot early.