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Massachusetts Trail Running Calendar 2025-2026

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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 2025-2026! Our updated list features 28 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

January 2026
Jan
25
Su

Dar Snowshoe Scramble

Trail Run 10 km
February 2026
Feb
7-8
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi 30 hr
March 2026
Mar
14
Sa

Ramsey's Run

Trail Run 5 km
Mar
21
Sa

Tarc to Hale and Back

Trail Run 4 mi 6 hr
April 2026
Apr
4
Sa

Tortoise and the Hare Trail Race

Trail Run 5 km 10 km
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
25
Sa

TARC Spring Classic

Trail Run 10 km Half Marathon Marathon 50 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
16
Sa

Free Spirit 50k

Trail Run 50 km
May
30
Sa

Wildcat 5K Trail Run-Walk-Wag

Trail Run 5 km
June 2026
Jun
7
Su

The Wine Run at Westport Rivers Vineyard & Winery

Trail Run 3 mi
Jun
13
Sa

Flat Rock Trail Race

Trail Run 5 mi 6 hr
July 2026
Jul
10-13
Fr - Mo

Notchview Ultra

Trail Run 6 hr 12 hr ... 48 hr 72 hr
Jul
11
Sa

TARC Blue Hills Skyline Trail Run

Trail Run 12 km
August 2026
Aug
8
Sa

Sweltering Summer Ultra

Trail Run 8 hr
Aug
8
Sa

Tarc Summer Classic

Trail Run 10 mi 50 km 40 mi