Darien close

Trail Running Calendar near Darien 2025-2026

Explore the top trail runs near Darien for 2025-2026! We've gathered 24 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
4
Saturday

Chasing Ciara's Light

Trail Run 5 km 12 km
Oct
5
Sunday

IBBC Trail Classic 5k

Trail Run 5 km
Oct
10
Friday

Tesla Hertz Run

Trail Run 10 mi 50 km ... 100 mi 150 mi
Oct
11
Saturday

Gemstone Sparkle Sprint 5k

Trail Run 5 km
Oct
12
Sunday

Paine to Pain Trail Half Marathon

Trail Run Half Marathon
Oct
12
Sunday

NSRF Great Pumpkin Dash Trail 5K

Trail Run 5 km
Oct
19
Sunday

Run The Farm - Katonah

Trail Run 5 mi
November 2025
Nov
2
Sunday

8 Hours At The Farm

Trail Run 4 mi 4 hr 8 hr
Nov
2
Sunday

People in Need - Day of the Dead 5k

Trail Run 5 km
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
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
29
Saturday

NSRF Leftover Turkey Trot 5K

Trail Run 5 km
Nov
30
Sunday

NSRF 50/50 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
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series