Peekskill close

Trail Running Calendar near Peekskill 2026-2027

Monthly updates for Peekskill

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

Explore the top trail runs near Peekskill for 2026-2027! We've gathered 30 exciting races in the area. Check out our detailed list below to find your next local race.

April 2026
Apr
4
Sa

Big Bear Squatch North

Trail Run 10 km 13 mi
Apr
12
Su

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
12
Su

Farm & Forest All-Terrain 5K

Trail Run 5 km
Apr
12
Su

IBBC Trail Classic 5K - Irvington

Trail Run 5 km
Apr
18
Sa

Conquer the Trail Race

Trail Run 8 km
Apr
26
Su

Leatherman's Loop

Trail Run 10 km
May 2026
May
2
Sa

Bear Mountain Trail Challenge

Trail Run 10 km Half Marathon 50 km
May
3
Su

Breakneck Point Trail Runs

Trail Run Half Marathon Marathon
May
9
Sa

Mother's Day REXtravaganza

Trail Run 4 mi 8 mi 11 mi
May
17
Su

Spring Run the Farm

Trail Run 5 mi
May
17
Su

C'mon Armageddon

Trail Run 5 mi 10 mi 50 km
June 2026
Jun
6
Sa

Rockwood Ramble 10K

Trail Run 10 km
July 2026
Jul
5
Su

Red Wing Trail Challenge

Trail Run 15 km 30 km 60 km
Jul
11
Sa

The Revolution

Trail Run 3 hr 6 hr 12 hr
August 2026
Aug
1
Sa

Ridge Reaper Trail Runs

Trail Run 25 km 50 km 50 mi
Aug
8
Sa

Interstate 17 - Closter, NJ

Trail Run 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
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi