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Trail Running Calendar near Milton 2025-2026

Explore the top trail runs near Milton for 2025-2026! We've gathered 86 exciting races in the area. Check out our detailed list below to find your next local race.

April 2025
Apr
5
Saturday

F.I.T. the Challenge OCR

Obstacle Run 3 mi
Apr
5
Saturday

Police and Fire 5k for Autism

3 mi
Apr
5
Saturday

Duxbury Half Marathon

13 mi
Apr
5
Saturday

The Reggie Lewis Track and Athletic Center Walk and Run

2 mi 4 mi
Apr
6
Sunday

Bailey's Run for Autism

5 km
Apr
6
Sunday

Linclusion 5K

5 km
Apr
6
Sunday

Race to Cure Sarcoma Boston

5 km
Apr
6
Sunday

Cohasset Road Race by the Sea

10 km
Apr
12
Saturday

Spring Fever 5K | 5M | 8H

Trail Run 5 km 5 mi 8 hr
Apr
12
Saturday

Black Excellence 5K

5 km
Apr
12
Saturday

Merrimack River Trail Race

Trail Run 10 mi
Apr
12
Saturday

Holliston High School Panther Prowl 5k

5 km
Apr
13
Sunday

Marblehead Half Marathon

13 mi
Apr
13
Sunday

Dirty Rabbit 5K

5 km
Apr
19
Saturday

TRUE Marathon

26 mi
Apr
19
Saturday

Lexington Lions Patriots Day 5 Mile Road Race

5 mi
Apr
20
Sunday

Run Through the Pines Half Marathon

5 km 13 mi
Apr
21
Monday

Boston Marathon

26 mi
Apr
26
Saturday

TARC Spring Classic

Trail Run 10 km 13 mi 26 mi 50 km
Apr
26
Saturday

Rally for Research

5 km
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