Trail Running Calendar Maryland 2026-2027

Challenge yourself on scenic singletrack at Rockburn Branch Park in the Mid Maryland Trail Festival, featuring a 50K and a 50K relay. Run six loops or join a team of 2 to 6 with options to run fewer loops and aid stations on course.

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.

Run scenic, tame trails along the Little and Middle Patuxent Rivers in Columbia, MD during a fun January race weekend. Choose 5K, 10K or half marathon distances and earn finisher medals, a long sleeve shirt and knit gloves.

The Delmarva Ultra Challenge is a 100K trail test in Pocomoke run as two 50K efforts, one night and one morning. A surprise night course and limited spots make this a gritty, tactical event for experienced ultrarunners.

Community driven 50K trail race through Pocomoke River State Park, featuring mostly flat single track and scenic river views. Volunteer run with stocked aid stations and a handmade ceramic mug for every finisher.

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 5K through forest trails at Wicomico Demonstration Forest in Parsonsburg, MD on February 21, 2026. Proceeds benefit 4STEPS therapeutic riding programs, making this debut trail race a great way to support riders and enjoy nature..

Run a scenic 10.5 mile loop around Saint Marys Lake and into Salem Forest in Leonardtown, MD with 17K, 34K, and 50K options. Enjoy mostly single track trails, a field limited to 100 runners, and pancakes at the finish.

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..

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.

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..

Explore a scenic 10 mile trail through laurel and pine in Pocomoke State Forest along Blades Road, with mossy singletrack and creek crossings. Bring your own cup or bottle as the race is cupless and offers one aid station.

Tackle the HAT Run 50K, a scenic and challenging trail race in Havre de Grace on March 21, 2026. Expect varied terrain, nearly 4,400 feet of climbing and a few stream crossings that keep the adventure real.

The Rosaryville Half Marathon will take place in Upper Marlboro on Saturday 28 March 2026. You can run between 5 and 21 kilometers.

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 is a timed trek around Deep Creek Lake at Wisp Resort with ridgeline climbs and panoramic lake views on 7 mile loops. Finish your distance within 10 hours to earn commemorative swag and enjoy a post trek celebration.

Join the Turtle Derby, a turtle themed 5K on brewery trails supporting Susquehannock Wildlife. Enjoy a wooden finisher medal, costume contests, awards, live music and on site beer.

Run the scenic Breeze Thru the Trees at Ruppert Nurseries in Gaithersburg, where a 5K and 1 mile fun run wind through a tree farm. Proceeds benefit the Montgomery County Children's Opportunity Alliance and early childhood programs.

Run to Remember at Piney Run Park offers scenic 5.25 mile loops with lake views and race options from a 5 Mile to 50K or the 8 Hour challenge scored by laps. Well stocked aid, swag and proceeds support youth programs and cancer research.