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!

December 2025
Dec
7
Sunday

Happy Holidays Half Merrython

5 km 13 mi
Dec
7
Sunday

Winter Classic

5 km
Dec
7
Sunday

Woo Jingle 5K

5 km
Dec
7
Sunday

Jingle Bell Half Marathon

5 km 13 mi
Dec
7
Sunday

Medfield Foundation Angel Run

5 km
Dec
13
Saturday

Mount Hood Nutcracker Challenge

Trail Run 2 mi 3 mi
Dec
14
Sunday

Somerville Jingle Bell Run

5 km
Dec
14
Sunday

Santa's Toy Trot 6-mile Road Race

2 mi 4 mi 6 mi
January 2026
Jan
1
Thursday

New Year's Day Hangover Classic

5 km 10 km
February 2026
Feb
7-8
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi 30 hr
Feb
14
Saturday

MV Winter Classic 20 Miler

10 mi 20 mi
March 2026
Mar
1
Sunday

Hyannis Marathon

10 km 13 mi 26 mi
Mar
15
Sunday

New Bedford Half Marathon

13 mi
Mar
28
Saturday

Fool's Dual Half Marathon

5 km 13 mi
April 2026
Apr
11
Saturday

Merrimack River Trail Race

Trail Run 10 mi
Apr
12
Sunday

Marblehead Half Marathon

13 mi
Apr
25
Saturday

TARC Spring Classic

Trail Run 10 km 13 mi 26 mi 50 km
Apr
26
Sunday

James Joyce Ramble 10 Km

10 km
May 2026
May
3
Sunday

Cahill 5k Race

5 km
May
3
Sunday

Twin Lights Half Marathon

13 mi
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