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Trail Running Calendar near Madison 2026-2027

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Explore the top trail runs near Madison for 2026-2027! We've gathered 41 exciting races in the area. Check out our detailed list below to find your next local race.

November 2026
Nov
14
Sa

SOMO Winter Trail Series

Trail Run 5 km 10 km 13 mi
Nov
15
Su

NYRR Cross Country Series

Trail Run 5 km
Nov
15
Su

Last Chance XC Championships

Trail Run 3 km 5 km 8 km
Nov
22
Su

FEAR Trail Fest

Trail Run 5 mi
Nov
26
Th

Inwood Hill Turkey Trot

Trail Run 5 km
Monthly updates for Madison

Get new running races (and updates) in your inbox every month.
Nov
28
Sa

Squatchy Leftovers Trail Race

Trail Run 5 km 10 km 25 km 50 km
December 2026
Dec
5
Sa

SOMO Winter Trail Series

Trail Run 5 km 10 km 13 mi
Dec
6
Su

PPTC Endurance Fest

Trail Run 50 km 50 mi
Dec
12
Sa

Morris Hot Cocoa 10k

Trail Run 5 km 10 km
January 2027
Jan
9
Sa

SOMO Winter Trail Series

Trail Run 5 km 10 km 13 mi
Jan
30
Sa

Frosty Squatchy

Trail Run 5 km
February 2027
Feb
14
Su

Squatchy Onesiefest 5K

Trail Run 2 mi 5 km
Feb
20
Sa

Febapple Frozen 50M

Trail Run 10 mi 20 mi 50 km 50 mi
March 2027
Mar
6
Sa

Squatchapple

Trail Run 11 mi 20 mi 50 km 50 mi
Mar
21
Su

Morris County Empanada Trail Run

Trail Run 5 km 10 km
May 2027
May
1
Sa

VCP 50K

Trail Run 50 km
May
16
Su

C'mon Armageddon

Trail Run 5 mi 10 mi 50 km
August 2027
Aug
14
Sa

Interstate 17 - Closter, NJ

Trail Run 17 mi
November 2027
Nov
27
Sa

Squatchy Leftovers Trail Race

Trail Run 5 km 10 km 25 km 50 km
January 2923
Jan
7
Th

Freezing Cold Hash Run FCH

Trail Run 2 mi 3 mi 5 mi
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