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Trail Running Calendar near Middletown 2025-2026

Explore the top trail runs near Middletown for 2025-2026! We've gathered 14 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
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 13 mi 50 km 50 mi 100 km
Apr
25-26
Sa - Su

Xterra New Jersey

Trail Run Triathlon 5 km 10 km ... 39 km Marathon
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
September 2026
Sep
19-20
Sa - Su

Wild Goose Trail Festival

Trail Run 10 km 13 mi ... 100 mi 36 hr
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 8 km 10 km