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

July 2026
Jul
25
Sa

Blue Crab Bolt Trail Run - Schaeffer Farms

Trail Run 3 mi 7 mi
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 4 mi 6 mi
Aug
15
Sa

MD Heat Trail Race

Trail Run 25 km 50 km
Aug
16
Su

MCRRC Groovin' Woodstock 7K

Trail Run 7 km
Aug
22
Sa

Tom LaMonica Memorial Trail Run

Trail Run 5 km
Aug
30
Su

High Rock Mountain Running Challenge

Trail Run 4 mi
September 2026
Sep
18
Fr

The Pemberton 24

Trail Run 5 km
Sep
26
Sa

River's Edge Endurance Challenge

Trail Run 5 km
Sep
26
Sa

Cancer Warriors 5k

Trail Run 5 km
Sep
27
Su

MoCo Dems 5K FunRun

Trail Run 5 km
October 2026
Oct
11
Su

Rick O'Donnell Memorial Ultra Challenge

Trail Run 5 mi
Oct
11
Su

Rocky Gap Trail Run

Trail Run 25 km 50 km
Oct
11
Su

Run like Michael

Trail Run 5 km
Oct
17
Sa

MCRRC Black Hill 10K

Trail Run 10 km
Oct
17
Sa

Boulder Dash at Pinesburg Quarry

Trail Run 5 km 5 mi
Oct
24
Sa

Patapsco Valley 50K

Trail Run 25 km 50 km
Oct
25
Su

Run the Vineyards Rocklands Farm 5K

Trail Run 5 km
November 2026
Nov
1
Su

Fire On The Mountain 50K Trail Race

Trail Run 25 km 50 km
Nov
7
Sa

Schaeffer Half Marathon and 10K Trail Run

Trail Run 3 mi 7 mi 14 mi
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