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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 60 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

August 2026
Aug
30
Su

UltraTrax Wachusett

Trail Run 7 mi 14 mi 21 mi 28 mi
September 2026
Sep
5
Sa

TARC Fall Classic

Trail Run 10 km Half Marathon ... 50 km 50 mi
Sep
5
Sa

Foot It for Felix 5K

Trail Run 5 km
Sep
27
Su

Run for Nature - Lowell

Trail Run 5 km 10 km
October 2026
Oct
4
Su

Groton Town Forest Trail Races

Trail Run 3 mi 10 mi
Oct
11
Su

Wayland / HFC Striders XC Festival

Trail Run 3 km 5 km
Oct
11
Su

BMS Athletic Booster Club 5K

Trail Run 3 mi
Oct
17
Sa

United We Move

Trail Run 5 km 10 mi
Oct
24
Sa

Womp Romp

Trail Run 10 mi 50 km
Oct
24
Sa

Pumpkin Pacer 5k

Trail Run 5 km
Oct
24
Sa

Mt. Tom Trail Race

Trail Run 5 km 10 km 25 km
Oct
25
Su

The Baystate Dirty Dog Trail Run

Trail Run 5 km
Oct
25
Su

Powisset Farm Trail Run - Fall

Trail Run 2 mi 3 mi 6 mi 9 mi
Oct
25
Su

Run for the Hills - Harvard

Trail Run 5 km
November 2026
Nov
7
Sa

TARC Stone Cat Trail Festival

Trail Run 10 km Half Marathon ... 50 mi 100 km
Nov
7
Sa

Race for DFL

Trail Run 4 mi
Nov
7
Sa

The Next Loop - New England

Trail Run 5 km 10 km ... 26 mi 50 km
December 2026
Dec
5
Sa

TARC Winter Classic

Trail Run 8 mi 32 mi 40 mi
Dec
12
Sa

Mount Hood Nutcracker Challenge

Trail Run 2 mi 4 mi
February 2027
Feb
6-7
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi
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