Trail Running Calendar Maryland 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.

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.

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..

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.

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.

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..

Run scenic single track around Saint Marys Lake near Leonardtown with 17K, 34K, and 50K options on a roughly 10.5 mile loop featuring rolling climbs, aid stations, timing, and finish line pancakes. Limited to 100 runners for a friendly trai..

Join the Bigfoot Endurance 5 and 10 Mile at Rockburn Branch Park on March 1 2026, with a team relay option. Get a long sleeve shirt, finisher medal and two post race beers while supporting Parkinson's research on scenic gravel and natural t..

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.

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.

Challenge yourself on the scenic B&A Trail in Severna Park with marathon or half marathon options on March 29, 2026. Enjoy USATF certified courses, friendly aid stations and a commemorative finisher medal.

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.

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 scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.

Run the Dash Through the Dirt May 16, 2026 at Carderock on the scenic C&O Canal towpath in Potomac MD. Choose 5k, 10k or half marathon on light gravel with chip timing, tech shirt and finisher coin. Proceeds benefit EOD Warrior Foundation.