Massachusetts Trail Running Calendar 2025-2026

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Explore the best trail runs in Massachusetts for 2025-2026! Our updated list features 214 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

May 2025
May
3
Saturday

7 Sisters Trail Race

Trail Run 12 mi
May
3
Saturday

Bulfinch Bee Run

5 km
May
3
Saturday

Dennis Chamber of Commerce 5k Road Race/Walk

5 km
May
3
Saturday

Lauren's Haven 5K Run/Walk

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
3
Saturday

Harbor Run

5 km
May
4
Sunday

Cahill 5k Race

5 km
May
4
Sunday

Dandelion Dash

Trail Run 5 km
May
4
Sunday

Step Up for Colleen 5K

5 km
May
4
Sunday

Worcester Cinco 5K

3 mi
May
4
Sunday

Twin Lights Half Marathon

13 mi
May
4
Sunday

Runway 5k - Northampton

5 km
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

Jack Rome Memorial 5K

5 km 10 km
May
4
Sunday

Walter Childs Marathon

13 mi 26 mi
May
4
Sunday

Groton Road Race

5 km 10 km
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