Massachusetts Trail Running Calendar 2025-2026

Header image

Explore the best trail runs in Massachusetts for 2025-2026! Our updated list features 146 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

May 2026
May
9
Saturday

Tarc Wapack and Back

Trail Run 21 mi 43 mi 50 mi
May
9
Saturday

Grafton Gazebo Road Race

5 km
May
9
Saturday

Barns & Blooms Half Marathon

13 mi
May
16
Saturday

Runnin' for a Cause, Not from the Cops

5 km
May
17
Sunday

Harpoon 5-Miler

5 mi
May
17
Sunday

Evan's Run

5 km
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series