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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!

November 2026
Nov
7
Sa

Stone Mill 50 Mile Run

Trail Run 50 mi
Nov
8
Su

Run Through the Grapevine

Trail Run 8 km
Nov
14
Sa

Rosaryville Veterans Day Trail Race

Trail Run 20 km 50 km
Nov
21
Sa

The Tuckahoe 25K

Trail Run 25 km
Nov
22
Su

Maryland Turkey Trot 10K

Trail Run 5 km 10 km
Nov
26
Th

Catonsville High School XC Turkey Trot

Trail Run 5 km
Nov
26
Th

VHTRC Turkey Chase

Trail Run 10 mi
January 2027
Jan
16
Sa

Phunt 25K/50K Trail Race

Trail Run 25 km 50 km
February 2027
Feb
20
Sa

4Steps Therapeutic Riding 5k

Trail Run 3 mi
Feb
27
Sa

Hashawha Hills

Trail Run 50 km
April 2027
Apr
10
Sa

Turtle Derby 5K Trail Race

Trail Run 5 km
Apr
24
Sa

C&O Canal 100

Trail Run 100 mi
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