Trail Races in Maryland

Browse 87 upcoming trail races in Maryland, soonest first. Each listing has the date, distance and a link to register.

87 races found

Showing 87 races. Try narrowing your search with a location, distance, surface, or date range to find the right race faster.

UltraTrail

The Pemberton 24

Sep 18, 2026Salisbury, MD

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13.1 Miles, 3.1 Miles, 1 MilesTrail

Annapolis RUN for The Light House

Sep 18, 2026Annapolis, MD

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Trail

POSTPONED UNTIL FALL OF 2027 - Climb to End Cancer - Historic Fort Ritchie presented by: WellAve Dermatology

Sep 19, 2026Cascade, MD

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3.1 MilesTrail

Sip and Stride 5K

Sep 19, 2026Prince Frederick, MD

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3.1 Miles, 6.2 Miles, 1 MilesRoad, Trail

Police Pace 5K, 10K, & 1 Miler

Sep 20, 2026Ellicott City, MD

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Trail

Hyattsville Cyclocross– Super Series

Sep 20, 2026Hyattsville, MD

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5K, 10KTrail

2026 Prelude 5k & 10k Walk/Run

Sep 26, 2026Glenn Dale, MD

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3 MilesTrail

Bull Run REUNION RUN 2026

Sep 26, 2026Parkton, MD

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3.11 Miles, 1 MilesTrail

Fox Trot 5K & 1Mile Bark in the Park

Sep 26, 2026Elkton, MD

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5KTrail

River's Edge Endurance Challenge

Sep 26, 2026Brunswick, MD

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10 Miles, 13.1 Miles, 20 MilesTrail

Run On The Rocks • 10M / Half / 20M

Sep 26, 2026Point Of Rocks, MD

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20 MilesTrailFeatured

Charm City Run 20 Miler

Sep 27, 2026Parkton, MD

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800m, 1600m, 2400mTrail

Greenbrier SwimFest

Sep 27, 2026Boonsboro, MD

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5KTrail

MoCo Dems 5K Fall FunRun

Sep 27, 2026Derwood, MD

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20 MilesTrail

Charm City Run 20-Miler presented by On

Sep 27, 2026Freeland, MD

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4 MilesTrail

Spook Hill Cider & Wine 4 Mile Run

Oct 1, 2026Burkittsville, MD

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5KTrail

Colleen's BA 5K in Collaboration with BARE

Oct 1, 2026Kensington, MD

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5.3 MilesTrail

Hart-Miller Island Run

Oct 3, 2026Essex, MD

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Trail

MCRRC Cabin John Kids' Run

Oct 3, 2026Bethesda, MD

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3.1 MilesTrail

Flutter Fest 5k

Oct 4, 2026Mechanicsville, MD

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Other race distances in Maryland

All races 5K 10K Half Marathon Marathon

Trail Races in other states

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