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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 47 exciting races across the region. Find your next race in Maryland below and join the running community at these great events!

April 2026
Apr
11
Sa

Turtle Derby 5K Trail Race

Trail Run 5 km
Apr
18
Sa

Run to Remember - Sykesville

Trail Run 5 mi 25 km 50 km 8 hr
Apr
19
Su

Spring Hops

Trail Run 5 km
Apr
25
Sa

C&O Canal 100

Trail Run 100 mi
May 2026
May
2
Sa

Farm Park Challenge

Trail Run 25 km 3 hr ... 6 hr 10 hr
May
6-27
We

Johnnycake Jolt Series

Trail Run 10 km
May
13
We

Johnnycake Jolt Series

Trail Run 10 km 40 km
May
16
Sa

Dash Through the Dirt Half

Trail Run 5 km 10 km Half Marathon
May
20
We

Johnnycake Jolt Series

Trail Run 10 km 40 km
May
27
We

Johnnycake Jolt Series

Trail Run 10 km 40 km
June 2026
Jun
6
Sa

Gary Brown Memorial C&O Canal Run

Trail Run 5 mi
Jun
27
Sa

Blue Crab Bolt Trail Run

Trail Run 5 km 10 km
Jun
28
Su

MCRRC XC on the Farm

Trail Run 5 km
July 2026
Jul
12
Su

BRRC Sweet Air Trail Race

Trail Run 7 mi
Jul
18
Sa

Endless Summer 6-Hour Run

Trail Run 6 hr
Jul
25
Sa

Blue Crab Bolt Trail Run - Schaeffer Farms

Trail Run 5 km 10 km
August 2026
Aug
1
Sa

Run the Vineyards Bohemia Manor Farm 8K

Trail Run 5 km 8 km
Aug
1
Sa

Blue Crab Bolt Trail Run - Little Bennett

Trail Run 5 km 10 km
Aug
15
Sa

MD Heat Trail Race

Trail Run 25 km 50 km
September 2026
Sep
18
Fr

The Pemberton 24

Trail Run 5 km