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Trail Running Calendar near Chester 2026-2027

Monthly updates for Chester

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

Explore the top trail runs near Chester for 2026-2027! We've gathered 19 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
31
Sa

Yeti or Not Snowshoe Invasion

Trail Run 5 km
February 2026
Feb
14
Sa

Squatchy Onesie Fest “5K-Marathon”

Trail Run 5 km
March 2026
Mar
29
Su

The Fool's Trek/Rogaine

Trail Run 10 hr
April 2026
Apr
4
Sa

Big Bear Squatch North

Trail Run 10 km 13 mi
Apr
19
Su

Brooklyn Cider House Spiked Apple 5K

Trail Run 5 km
Apr
25
Sa

Squatchywaska Mountainfest

Trail Run 10 mi 25 km
Apr
25
Sa

Wawayanda Trail Fest

Trail Run Half Marathon 50 km 50 mi 100 km
Apr
25
Sa

Xterra New Jersey

Trail Run Triathlon
May 2026
May
3
Su

Breakneck Point Trail Runs

Trail Run Half Marathon Marathon
May
17
Su

C'mon Armageddon

Trail Run 5 mi 10 mi 50 km
May
17
Su

Run like the Wind 5K - Ellenville

Trail Run 5 km
August 2026
Aug
9
Su

Thunder Chicken Squatch

Trail Run 5 km 10 km 17 mi
Aug
15
Sa

Fabulous Fahnestock Trail Races

Trail Run 6 mi 25 km 50 km
September 2026
Sep
19-20
Sa - Su

Wild Goose Trail Festival

Trail Run 10 km 13 mi ... 100 mi 36 hr
Sep
19
Sa

Hook Mountain Ultra

Trail Run 27 mi 50 mi
October 2026
Oct
18
Su

Big Bear SquaTCh South

Trail Run 10 km 13 mi
Oct
18
Su

Clinton Road Zombie Run

Trail Run 5 km 10 km
November 2026
Nov
7
Sa

Pocantico Hills Marathon

Trail Run Half Marathon Marathon
Nov
29
Su

Rob's Trail Run

Trail Run 5 km