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Trail Running Calendar near Holliston 2025-2026

Explore the top trail runs near Holliston for 2025-2026! We've gathered 51 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
7
Sunday

Beantown Marathon

26 mi
Sep
7
Sunday

Title 9 Women's Triathlon

Triathlon
Sep
14
Sunday

Ride for Liv / Run for Liv

5 km 10 km
Sep
14
Sunday

Downtown 5K

5 km
Sep
20
Saturday

Bedford Day 5K

5 km
Sep
20
Saturday

St. Mary’s 5K

5 km
Sep
21
Sunday

Together in TEAL Boston

5 km
Sep
27
Saturday

Colin's Joy Project 5K

5 km
Sep
27
Saturday

Run Medford

2 mi 5 km 5 mi
Sep
28
Sunday

La Vita e Bella 5K

5 km
Sep
28
Sunday

Canton Road Race 5k/10k

5 km 10 km
October 2025
Oct
5
Sunday

Groton Town Forest Trail Races

Trail Run 3 mi 9 mi
Oct
5
Sunday

Gloria Gemma 5K

5 km
Oct
5
Sunday

Fall Classic - Cambridge

5 km
Oct
5
Sunday

Def Dash 5k

5 km
Oct
5
Sunday

Houghton's Pond Trail Race

Trail Run 3 mi 7 mi
Oct
12
Sunday

Austin Reardon Memorial 5K

5 km
Oct
12
Sunday

Boston Firefighters Memorial Road Race

10 km
Oct
19
Sunday

Scaredy Cat 5K

5 km
Oct
19
Sunday

Run the Res 5k

5 km
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