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Maryland Trail Running Calendar 2025-2026

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Explore the best trail runs in Maryland for 2025-2026! Our updated list features 31 exciting races across the region. Find your next race in Maryland below and join the running community at these great events!

September 2025
Sep
19
Friday

The Pemberton 24

Trail Run 5 km
Sep
20
Saturday

Cancer Warriors 5k

Trail Run 5 km
Sep
20
Saturday

Bull Run Reunion Run

Trail Run 3 mi
Sep
21
Sunday

The Kellie Thompson Shiley 5k

Trail Run 5 km
Sep
27
Saturday

Lake & Leaf Shuffle

Trail Run 6 mi 12 mi
Sep
27
Saturday

River's Edge Endurance Challenge

Trail Run 5 km 3 hr 6 hr
October 2025
Oct
11
Saturday

MoCo Dems 5K FunRun

Trail Run 5 km
Oct
12
Sunday

Rocky Gap Trail Run

Trail Run 25 km 50 km
Oct
12
Sunday

Rick O'Donnell Memorial Ultra Challenge

Trail Run 5 mi 4 hr 8 hr
Oct
18
Saturday

Coastal 5K Run

Trail Run 2 mi 5 km
Oct
18
Saturday

Boulder Dash at Pinesburg Quarry

Trail Run 5 km 5 mi
Oct
19
Sunday

The Husky Run 5K

Trail Run 5 km
Oct
25
Saturday

Patapsco Valley 50K

Trail Run 25 km 50 km
Oct
25
Saturday

RTB Fair Winds 5k

Trail Run 5 km
Oct
25
Saturday

North Point Fright Night 5K & Haunted Trail

Trail Run 5 km
November 2025
Nov
2
Sunday

Fire On The Mountain 50K Trail Race

Trail Run 25 km 50 km
Nov
8
Saturday

Stone Mill 50 Mile Run

Trail Run 50 mi
Nov
8
Saturday

Rosaryville Veterans Day Trail Race

Trail Run 20 km 50 km
Nov
8
Saturday

Schaeffer Half Marathon and 10K Trail Run

Trail Run 7 mi 13 mi
Nov
22
Saturday

The Tuckahoe 25K

Trail Run 25 km
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