Trail Running Calendar Maryland 2026-2027

Tackle a scenic 50K trail ultramarathon at Rockburn Branch Park on six wooded loops of about 5.2 miles each. Race solo or as a team of 2 to 6 with stocked aid stations and a friendly festival atmosphere.

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.

Join the Little Patuxent River Half Marathon, 10K and 5K in Columbia MD on Jan 31 to Feb 1, 2026 along gentle trail sections by the Patuxent. This edition is sold out, but finishers get shirts, medals and knit gloves.

Delmarva Ultra Challenge 100K in Pocomoke MD pairs an overnight 50K with a morning 50K on the Algonquin course. Combine times across both runs for a rewarding and mysterious two day trail test.

Run a scenic 50K at Milburn Landing in Pocomoke River State Park, Maryland, mostly on trail with sandy sections and winter weather possible. Community supported aid stations, an 8 hour cutoff, and handmade mugs for finishers.

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.

Challenge a scenic 7 mile trail through Cromwell Valley Park with rolling hills and mostly single track, capped by a fast downhill finish. Join on Feb 8, 2026 to race, enjoy post race food and beer, and support park programs and scholarship..

Celebrate Valentine’s Day with a fun and friendly 5K at Kinder Farm Park in Millersville on Feb 14, 2026. Enjoy a mostly flat loop with gentle hills, chip timing, and awards for top finishers in a welcoming community race.

Hit the forest trails in Parsonsburg for the 4STEPS Therapeutic Riding 5K on Saturday, February 21, 2026. Enjoy a scenic first time 5K through Wicomico Demonstration Forest while supporting therapeutic riding programs for riders with specia..

Discover scenic trails around Saint Marys Lake near Leonardtown, MD with 17K, 34K or 50K on one to three laps through Salem Forest. Limited to 100 runners, this intimate event has rugged single track, lake views and on course aid.

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.

Join the Bigfoot Endurance Trail Race at Rockburn Branch Park in Elkridge on March 1, 2026 with 5 mile, 10 mile and two person relay options on scenic trails. Get a long sleeve shirt, finisher medal, post race beers and support Parkinson's..

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.

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..

Run a 10 mile trail through the Hudson Tarr tract of Pocomoke State Forest in Pocomoke Maryland on March 15, 2026. Expect creek crossings, a single aid station, limited parking, and a rugged backcountry vibe for adventurous trail runners.

Tackle the HAT Run 50K ultramarathon in scenic Havre de Grace, Maryland on March 21, 2026. Expect winding single track, nearly 4,400 feet of climbing and several stream crossings that may get your feet wet.

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..

Run through the woods and open fields of Rosaryville State Park with half marathon, 10K and 5K trail options plus virtual entries for March 28, 2026. Enjoy twisty but smooth, mostly flat trails hosted by EX2 Adventures.

Hit the scenic B&A Trail in Severna Park on March 29, 2026 with marathon and half marathon options, the marathon a Boston qualifier. Enjoy a mostly flat rails to trails route, generous aid, a finisher medal and participant apparel.

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.