Massachusetts Trail Running Calendar 2025-2026

Header image

Explore the best trail runs in Massachusetts for 2025-2026! Our updated list features 181 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

September 2025
Sep
7
Sunday

Title 9 Women's Triathlon

Triathlon
Sep
7
Sunday

North Shore Runfest

10 km
Sep
7
Sunday

Wicked Mudder

Trail Run 5 km
Sep
14
Sunday

Ride for Liv / Run for Liv

5 km 10 km
Sep
14
Sunday

Half Marathon-by-the-Sea

13 mi
Sep
14
Sunday

The Wine Run at Westport Rivers Vineyard & Winery

Trail Run 3 mi
Sep
14
Sunday

Buzzard's Bay Sprint Triathlon

Triathlon
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
28
Sunday

PortRun Half Marathon

5 km 13 mi
Sep
28
Sunday

La Vita e Bella 5K

5 km
Sep
28
Sunday

Run for Nature - Lowell

Trail Run 5 km 10 km
October 2025
Oct
4
Saturday

Fast and Furriest 5K Run

5 km
Oct
5
Sunday

Covered Bridge Classic

10 km
Oct
5
Sunday

Run Stanley

5 km
Oct
5
Sunday

Nicole Podkowa 5K

5 km
Oct
5
Sunday

Groton Town Forest Trail Races

Trail Run 3 mi 9 mi
Oct
5
Sunday

Fall Classic - Cambridge

5 km
Articles
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series
Stride with Confidence: A Comprehensive Guide to Saucony Running Shoes
Essential Running Form Techniques for Enhanced Performance and Injury Prevention