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Trail Running Calendar near Winchester 2025-2026

Explore the top trail runs near Winchester for 2025-2026! We've gathered 129 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
3
Saturday

Bulfinch Bee Run

5 km
May
3
Saturday

Cancer Doesn't Care But WE Do 5K

5 km
May
3
Saturday

St. Stephen's Armenian Elementary School 5k

5 km
May
4
Sunday

Cahill 5k Race

5 km
May
4
Sunday

Step Up for Colleen 5K

5 km
May
4
Sunday

Twin Lights Half Marathon

13 mi
May
4
Sunday

Emma's Run

2 mi 5 mi
May
4
Sunday

Kick in for Kids 5K Road Race

5 km
May
4
Sunday

Lead the Way 5K

5 km
May
4
Sunday

Charles River Marathon

26 mi
May
4
Sunday

Groton Road Race

5 km 10 km
May
4
Sunday

Run Like a Maverick

5 km
May
4
Sunday

Miles for Maura

5 km
May
4
Sunday

Gator Gallop 5K

5 km
May
10
Saturday

Run. Walk. United for Mental Health 5K

5 km
May
10
Saturday

Stride Along the Tide 5K

5 km
May
10
Saturday

Boston Marine Corps Honor Run

5 km
May
10
Saturday

Saint Catherine of Siena School 5K

5 km
May
11
Sunday

Melrose Run For Women

3 mi
May
11
Sunday

Moms' Run - Somerville

5 km
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