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Trail Running Calendar near New Canaan 2025-2026

Explore the top trail runs near New Canaan for 2025-2026! We've gathered 20 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
2
Sunday

8 Hours At The Farm

Trail Run 4 mi 4 hr 8 hr
Nov
2
Sunday

Woodbridge Trail Run

Trail Run 2 mi 4 mi
Nov
8
Saturday

Pocantico Hills Marathon

Trail Run Half Marathon Marathon
Nov
8
Saturday

Veterans Day Cross Country Run

Trail Run 4 km
Nov
9
Sunday

Raven Rocks 10k

Trail Run 10 km
Nov
9
Sunday

Taconic Road Runners FDR Park Cross County Run

Trail Run 6 km
Nov
9
Sunday

USATF-Long Island 8K

Trail Run 8 km
Nov
15
Saturday

NSRF Long Island Turkey Trail Trot 5K

Trail Run 5 km
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
23
Sunday

Head for the Hilltop 5K

Trail Run 5 km
Nov
29
Saturday

NSRF Leftover Turkey Trot 5K

Trail Run 5 km
December 2025
Dec
13
Saturday

Frosty Forest 5K

Trail Run 5 km
Dec
13-14
Sa - Su

SRC Presents: a Backyard Ultra

Trail Run 4 mi
April 2026
Apr
12
Sunday

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
25
Saturday

Lake Mohegan Women's Trail Race

Trail Run 5 km 10 km 4 hr
Apr
26
Sunday

Leatherman's Loop

Trail Run 10 km
May 2026
May
2
Saturday

VCP 50K

Trail Run 50 km
May
17
Sunday

Spring Run the Farm

Trail Run 5 mi
August 2026
Aug
8
Saturday

Interstate 17 - Closter, NJ

Trail Run 17 mi
November 2026
Nov
21
Saturday

Storybook Half Marathon

Trail Run 13 mi
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