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Trail Running Calendar near Clayton 2025-2026

Explore the top trail runs near Clayton for 2025-2026! We've gathered 38 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
12
Sunday

Bowers Heritage Day 5k

5 km
Oct
12
Sunday

Chestertown Challenge Half Marathon

5 km 13 mi
Oct
12
Sunday

Tender Hearts 5K

5 km
Oct
18
Saturday

Delaware Trail Fest

Trail Run 12 km 24 km 12 hr
Oct
18
Saturday

CompleteCare Foundation Halloween Bone Run

5 km
Oct
19
Sunday

Fox Trot 5K Bark in the Park

5 km
Oct
25
Saturday

Hot Mess Trail Races

Trail Run 13 mi 6 hr
Oct
26
Sunday

Sheldon Shuffle 5K

5 km
November 2025
Nov
1
Saturday

Delaware School for the Deaf 5k Run/Walk

5 km
Nov
8
Saturday

Harvest Hustle - Camden

5 km
Nov
15
Saturday

Shrewsbury Fall Run

5 km
Nov
28
Friday

#OptOutside Black Friday Fun Run

5 km
Nov
29
Saturday

Milford Cross Country Booster Reindeer Stampede 5k

Trail Run 5 km
December 2025
Dec
6
Saturday

Run Like The Dickens 5K

5 km
Dec
28
Sunday

Autumn Arch Winter Warmer

5 km
May 2026
May
9
Saturday

Savage Race - Maryland Spring

Obstacle Run 3 mi 7 mi
May
30
Saturday

Conquer The Canal

5 km 10 km 13 mi 26 mi
September 2026
Sep
5
Saturday

Savage Race - Maryland Fall

Obstacle Run 3 mi 7 mi
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