Trail Running Calendar Maryland 2025-2026

Tackle 50 miles of scenic single track along Seneca Greenway and Muddy Branch in Montgomery Village, MD. Expect rolling forest terrain, small stream crossings, and a community minded field for an unforgettable trail ultramarathon experience..

Tackle the Bobcat Trail Run, an 11 mile out and back through scenic Catoctin trails at Cunningham State Park on November 8, 2025. Expect rugged singletrack, a steep climb called Bobs Hill, an aid station at the turnaround and a cotton tee.

Run the 16th annual Rosaryville Veterans Day Trail Race at Rosaryville State Park with 50K and 20K routes through woods and meadows on rolling single track trails. Limited to 250 runners with aid stations and awards.

Enjoy fall trail racing at Button Farm Living History Center in Germantown, MD with a half marathon, 10K, 5K and a free kids race benefiting Interfaith Works. Expect twisty singletrack, open farm field views, medals, post race food and awar..

Tuckahoe 25k in Queen Anne Maryland is a scenic trail run with runnable hills and rooty, muddy sections. Three aid stations and event swag await finishers on Saturday, November 22 for a fun, rugged autumn challenge.

Celebrate Thanksgiving at the 21st Annual Catonsville High School XC Turkey Trot with a cross country style 5K and 1 Mile Family Fun Run in Catonsville, Maryland. Proceeds support the CHS cross country program.

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.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

Enjoy a scenic trail run along the Little and Middle Patuxent rivers in Columbia, Maryland. Choose from a half marathon, 10K or 5K on Jan 31 to Feb 1, 2026 at the Guilford Pratt Truss Bridge for a tame and rewarding trail experience.

Run the Mid Maryland Trail Festival at Rockburn Branch Park in Elkridge, MD, a scenic 50K on wooded trails made up of six loops of about 5.18 miles each. Solo runners or teams up to six can tackle the full distance or share loops in a relay..

Patriotic Pursuit at Williamsport Park offers 5k, 10k and half runs along a flat scenic C&O Canal Trail beside the river. Chip timed with finisher medal, tech shirt and virtual option supporting Semper Fi & America's Fund.

The Algonquin 50K is a community driven nonprofit trail race at Pocomoke River State Park starting and finishing at Milburn Landing. Expect mostly flat sandy trails, well stocked aid stations, and a friendly low key ultrarunning atmosphere.

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..

Explore a scenic loop around Saint Marys Lake and Salem Forest with 17K, 34K and 50K options on mostly single track trails and about 500 ft of climb per lap. Limited to 100 runners, with pancakes served at the finish.

Hit the trails at Rockburn Branch Park for the Bigfoot Endurance 5 and 10 mile trail race with solo or relay options and easy to moderate terrain. Enjoy a long sleeve race shirt, finisher medal, and support Parkinsons research.

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.

Test your limits at the Dark Side 8 Hour Ultra in Little Bennett Park, Clarksburg. You have eight hours to run as many 5.5 mile loops on scenic single track trails as you like, with hearty on course aid and a post race meal to refuel.

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 the HAT Run 50K in Havre de Grace, Maryland, a scenic trail challenge with rolling single track, open fields and nearly 4,400 feet of climbing. Expect stream crossings and a rewarding day on rugged, looped trails.

Test your endurance on a 2.5 mile loop at the Genesee Valley Outdoor Learning Center in Parkton, MD, with 6, 12 and 24 hour options for solo and team runners. Enjoy farm road and grass field terrain, camping, pacer options and on site suppo..