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Trail Running Calendar near Orange 2025-2026

Explore the top trail runs near Orange for 2025-2026! We've gathered 31 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
11-12
Sa - Su

Midstate Massive Ultra Trail

Trail Run 50 km 50 mi 100 mi
Oct
19
Sunday

Happy Valley Half Marathon

5 km 13 mi
November 2025
Nov
1
Saturday

MDS Run~Walk~Smile

10 km
Nov
2
Sunday

Western Mass 10

5 km 10 mi
Nov
8
Saturday

Orange Turkey Trot

5 km
Nov
8
Saturday

Race for DFL

Trail Run 4 mi 50 mi
Nov
22
Saturday

Roadtown Turkey Trot

5 km
Nov
27
Thursday

Holden Turkey Trot

5 km
May 2026
May
3
Sunday

Runway 5k - Northampton

5 km
May
9
Saturday

Tarc Wapack and Back

Trail Run 21 mi 43 mi 50 mi
August 2026
Aug
1
Saturday

Savage Race - Boston

Obstacle Run 3 mi 7 mi
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