Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 69 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
November 2026
Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.
A 50 mile trail race in Montgomery Village, Maryland on November 7, 2026 that follows the Seneca Greenway and Muddy Branch trails over forested single track terrain.
A community fundraising run in Cumberland along the GAP Trail offering 10K, 5K and a 1K fun run, with team results and scholarships for students.
A benefit run and walk along the Patuxent River supporting conservation, with USATF-certified 5K and 10K courses and a 3K fun walk.
An 11 mile out and back trail race in Cunningham State Park, Thurmont MD, on the Catoctin and Cat Rock trails with a single aid station at the 5.5 mile turnaround.
Trail 5k and 10k at Rock Creek Regional Park benefiting The Rock Creek Foundation with chip timing, medals, shirts and a virtual option.
Trail run, ruck, and walk at Heroes Ridge on November 7, 2026 with 10K, 5K and 1 mile options plus burpee challenges; proceeds benefit Operation Second Chance.
A scenic cross country 8K at Linganore Winecellars in Mt Airy, MD on November 8, 2026, featuring post race refreshments, awards and live music.
A scenic 5K at Milburn Orchards in Elkton on November 8, 2026, across orchard and farm trails with a portion of proceeds donated to local organizations.
A self timed 5k from Made Me Mine in Abingdon with walking option, stroller friendly course and parking at Constant Friendship Shopping Center.
Trail races in Rosaryville State Park on November 14, 2026 offering 50K and 20K on mostly single track with aid stations, drop bags, and time limits.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A marathon weekend in Brunswick MD featuring a USATF certified full marathon, a half marathon and a Veterans Challenge 5K along the Potomac and C&O Canal.
A free 5K cross country at Herring Run Park on November 15, 2026, with mixed terrain, river crossings, and donations accepted for local scholarships and park support.
A 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
Point to point 50.2 miles in Washington County, Maryland, running from Boonsboro along the Appalachian Trail and the C&O Canal to Williamsport.
25K trail race in Queen Anne, MD on November 21, 2026 with mostly single track, three stocked aid stations, awards for top finishers, and no refunds if canceled.
Three distances on the C&O Canal towpath from Great Falls Tavern with live GPS tracking, a capped field, and scratch-made donuts at the finish.
A 5k and 10k held on the C&O Canal at Carderock with chip timing, medals, shirts, a virtual option, and proceeds benefiting Project Pink Tax.