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Massachusetts Trail Running Calendar 2026-2027

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Monthly updates for Massachusetts

Get new running races (and updates) in your inbox every month.

Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 51 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

April 2026
Apr
4
Sa

Tortoise and the Hare Trail Race

Trail Run 3 mi 6 mi
Apr
11
Sa

Merrimack River Trail Race

Trail Run 10 mi
Apr
11
Sa

Spring Fever 5K | 5M | 8H

Trail Run 5 km 5 mi
Apr
12
Su

F.O.R. 5K Trail Race

Trail Run 5 km
Apr
25
Sa

TARC Spring Classic

Trail Run 10 km 13 mi 26 mi 50 km
Apr-Oct
25-24
Sa

Farm to Trail 5K Series

Trail Run 5 km
Apr
25
Sa

Radish Rambler 5k

Trail Run 5 km
May 2026
May
2
Sa

7 Sisters Trail Race

Trail Run 12 mi
May
3
Su

Dandelion Dash

Trail Run 5 km
May
3
Su

Cape Cod Trail Race

Trail Run 10 km 20 km 30 km
May
9
Sa

Tarc Wapack and Back

Trail Run 22 mi 43 mi 50 mi
May
9
Sa

Watuppa Trail Races

Trail Run 10 km 30 km 50 km
May
16
Sa

Free Spirit 50k

Trail Run 50 km
May
16-17
Sa - Su

Steel Rail Races

Trail Run 8 km 13 mi 26 mi
May
16
Sa

Tails & Trails State Forest Run

Trail Run 5 mi 25 km 50 km
May
16
Sa

FBRTC 5K Trail Race

Trail Run 5 km
May
16
Sa

Trillium Spring 5k

Trail Run 5 km
May
17
Su

Trav's Trail Run

Trail Run 2 mi 3 mi
May
20-21
We - Th

4K Trail Run

Trail Run 4 km
May
25
Mo

Powisset Farm Trail Run - Spring

Trail Run 2 mi 3 mi 6 mi 9 mi
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