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Trail Running Calendar near Winchester 2025-2026

Explore the top trail runs near Winchester for 2025-2026! We've gathered 78 exciting races in the area. Check out our detailed list below to find your next local race.

April 2025
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
19
Saturday

TRUE Marathon

26 mi
Apr
19
Saturday

Ipswich Ale Half Marathon

13 mi
Apr
19
Saturday

Lexington Lions Patriots Day 5 Mile Road Race

5 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
Apr
26
Saturday

Not a Walk in the Park 5K

5 km
Apr
26
Saturday

Winthrop Little League 5k

5 km
Apr
26
Saturday

Radish Rambler 5k

Trail Run 5 km
Apr
26
Saturday

Muddy Paws 5k

5 km
Apr
27
Sunday

Canton Public Library 5K

5 km
Apr
27
Sunday

Greater Beverly YMCA Rhino Run 10K

10 km
Apr
27
Sunday

Run BXB

5 km
Apr
27
Sunday

The Bionic 5K

5 km
May 2025
May
3
Saturday

Bulfinch Bee Run

5 km
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