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Maryland Trail Running Calendar 2026-2027

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Monthly updates for Maryland

Get new running races (and updates) in your inbox every month.

Explore the best trail runs in Maryland for 2026-2027! Our updated list features 55 exciting races across the region. Find your next race in Maryland below and join the running community at these great events!

April 2026
Apr
4
Sa

Wild Trail 10K - Thurmont

Trail Run 5 km 10 km
Apr
11
Sa

UltraTrax Wisp

Trail Run 7 mi 14 mi 21 mi 28 mi
Apr
11
Sa

Turtle Derby 5K Trail Race

Trail Run 5 km
Apr
12
Su

Care Packages at Carderock

Trail Run 5 km 10 km 13 mi
Apr
18
Sa

Run to Remember - Sykesville

Trail Run 5 mi 25 km 50 km
Apr
18
Sa

Gunpowder Keg Ultra

Trail Run 25 km 50 km
Apr
19
Su

Spring Hops

Trail Run 5 km
Apr
25-26
Sa - Su

C&O Canal 100

Trail Run
Apr
26
Su

Mount Aetna Adventist School's Fun Trail Run

Trail Run 3 km 5 km
May 2026
May
2
Sa

Farm Park Challenge

Trail Run 25 km 3 hr ... 6 hr 10 hr
May
2
Sa

Run Rock Creek 10K

Trail Run 5 km 10 km
May
3
Su

Spencerville Adventist Academy Cross Country 5K

Trail Run 3 mi
May
3
Su

Run for Preservation

Trail Run 5 km
May
6-27
We

Johnnycake Jolt Series

Trail Run 10 km
May
9
Sa

Gunpowder Trailfest

Trail Run 5 km 13 km 25 km
May
13
We

Johnnycake Jolt Series

Trail Run 10 km
May
16
Sa

Dash Through the Dirt Half

Trail Run 5 km 10 km Half Marathon
May
16
Sa

Ed Poling Memorial PA Challenge

Trail Run 10 mi 20 mi
May
16-30
Sa

Ed Poling Memorial Hike for Hunger & Hope

Trail Run 3 mi 7 mi 10 mi 20 mi
May
16-17
Sa - Su

To Break Boundaries 24 Hour Ultra Trail

Trail Run 22 mi
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