Trail Running calendar near Little Orleans 2026-2027

Run the Patriotic Pursuit on Jan 31, 2026 at Williamsport Park: chip timed 5k, 10k and half marathon along a flat gravel C&O Canal trail. Medal, technical shirt and virtual option included; proceeds benefit Semper Fi & America's Fund.

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 a scenic trail 5k or 10k at The Winery at Bull Run with chip timed results, a finisher medal, tech shirt and a complimentary glass of wine. Proceeds support the Manassas Battlefield Trust.

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..

Run a scenic 50 km trail at Hashawha Environmental Center near Westminster MD on Feb 28, 2026, featuring rolling hills, stream crossings and two big loops. Expect runnable single track, ample climbing and warm post race hospitality.

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.

Run scenic single track trails at Seneca Creek State Park in Gaithersburg March 7, 2026 with the MCRRC Seneca Creek Greenway Trail Marathon and 50K. Finish at the marathon or keep going to earn a 50K medal amid beautiful creekside terrain.

A vineyard 3k and 5k on a 1 km loop course at Creek’s Edge Winery with lap-based routes, on-course water stations, chip timing, a post-race glass of wine, and virtual participation available.

Run the Smoketown Brewery 5k or 10k in Brunswick MD on March 8, 2026, a flat out and back on light gravel. Virtual entries and walkers welcome, with chip timing, a finisher medal, tech shirt and beer while supporting Wear Blue Run to Rememb..

A free International Women’s Day endurance day at Beaverdam Reservoir Park featuring a 7.5-mile loop and varied trail surfaces. The event centers women, offers course support through sunset, and focuses on movement and mutual support.

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.

Run among saplings and open fields in the Breeze Thru The Trees 5K or enjoy a relaxed 1 mile fun run on Ruppert Nurseries' scenic tree farm in Gaithersburg. Proceeds benefit the Montgomery County Children's Opportunity Alliance to expand ea..

A 50 mile trail run in early April that follows trails near the Occoquan River and Bull Run in Clifton, Virginia, passing large bluebell stands and noting local Civil War sites. The 2026 race is the 32nd running.

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.

Join the Trail Demon 5k and 10k at Dirt Farm Brewing in Bluemont, VA on April 4, 2026, with in person or virtual entries. Expect technical forest trails, a finisher medal, tech shirt, chip timing and a post race beer.

Run the Dirty Kiln Trail Races at Canoe Creek State Park in Hollidaysburg PA on April 11, 2026 with a 10K or hilly half marathon. Expect singletrack, stream crossings and muddy sections on this volunteer run event.

UltraTrax Wisp at Wisp Resort on April 11, 2026 offers 7, 14, 21, and 28 mile loop options across singletrack and ski trails, optional 10/20/35 lb rucks, a 10-hour finish window, and finisher gear including a patch and shirt.

Run rugged trails with creek crossings and climbs at Buck Ridge Burn in Pine Grove Furnace State Park on April 12, 2026. Choose a half marathon, 10K, 5K or virtual option and enjoy small fields, handmade medals and a finisher coaster.

Run to Remember on April 18, 2026 at Piney Run Park in Sykesville offers looped trail races from 50K to a 5 miler and an 8 hour challenge. Honor club members while supporting youth programs, a scholarship and cancer research.

Experience a scenic 5k atop a ridge in apple country with cross country terrain, orchard views and a post race wine pour. Family friendly with virtual options, the event supports Nik's Wish and offers fun keepsakes for finishers.