Upcoming trail races in Maryland

20 trail races are coming up in Maryland, out of 173 races on the statewide calendar. Compare dates, distances and locations, then get ready with a personalized training plan.

20 upcoming races

September 2026

Sep 18, 2026The Pemberton 24📍 Salisbury, MD24 h
Sep 19, 2026Old Bay XC Open 6k📍 Stevensville, MD3.7 mi
Sep 20, 2026The Kellie Thompson Shiley 5k and Family Fun Run📍 Stevensville, MD3.1 mi · 1 mi

October 2026

Oct 11, 2026Rick O'Donnell Memorial 5.22 Mile & Ultra Challenge📍 Boonsboro, MD5 mi · 4 h · 8 h
Oct 11, 2026Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge📍 Mount Airy, MD5 mi · 4 h · 8 h
Oct 11, 2026Rocky Gap 25K, 50K, Relay Trail Run📍 Flintstone, MD16.1 mi · 32.2 mi
Oct 24, 2026Patapsco Valley 50K📍 Baltimore, MD15.5 mi · 31.1 mi
Oct 31, 2026Mackyard Ultra📍 Towson, MD0 mi

November 2026

Nov 1, 2026Fire on the Mountain 50K Trail Race📍 Little Orleans, MD15.5 mi · 31.1 mi
Nov 7, 2026MCRRC Stone Mill 50 Mile Run📍 Montgomery Village, MD50 mi
Nov 7, 2026Schaeffer Half Marathon and 10K Trail Run📍 Germantown, MD3.2 mi · 6.7 mi · 13.5 mi
Nov 21, 2026JFK 50 Mile📍 Funkstown, MD50 mi
Nov 21, 2026The Tuckahoe 25k📍 Queen Anne, MD15.5 mi

December 2026

Dec 6, 2026Stocking Suffer 8-Hour Endurance Run📍 Stevensville, MD8 h

February 2027

Feb 27, 2027Hashawha Hills 50 km Trail Run📍 Westminster, MD31.1 mi

March 2027

Mar 20, 2027HAT Run 50k📍 Havre de Grace, MD31.1 mi

April 2027

Apr 24, 2027C&O Canal 100📍 Brunswick, MD100 mi

June 2027

Jun 5, 2027The More Miles Last One Standing Challenge📍 Brunswick, MD4.2 mi · 1 mi

July 2027

Jul 11, 2027Sweet Air Trail Run📍 Baltimore, MD6.8 mi

August 2027

Aug 1, 2027Groovin’ Woodstock 7K📍 Beallsville, MD4.3 mi

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