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Trail Running Calendar near Danbury 2026-2027

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

August 2026
Aug
15
Sa

Fabulous Fahnestock Trail Races

Trail Run 6 mi 25 km 50 km
Aug
23
Su

Raptor Ridge

Trail Run 7 mi
September 2026
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
October 2026
Oct
3-4
Sa - Su

Forbidden Forest 30 Hour Ultra Run

Trail Run Backyard Ultra 26 mi 50 km ... 100 km 100 mi
Monthly updates for Danbury

Get new running races (and updates) in your inbox every month.
Oct
4
Su

Highlander Heavy Half

Trail Run 14 mi
Oct
10
Sa

Gemstone Sparkle Sprint 5k

Trail Run 5 km
Oct
10
Sa

Rocky's 5K

Trail Run 5 km
Oct
17
Sa

Tom Centinaro Memorial "Dam" Race

Trail Run 4 mi
Oct
24
Sa

Cheshire Community YMCA 5K Harvest Trail Run

Trail Run 5 km
Oct
25
Su

Run The Farm - Katonah

Trail Run 5 mi
Oct
25
Su

Castle to River Run

Trail Run 5 km Half Marathon
Oct-Nov
31-1
Sa - Su

Fall Back Into The Trails Series

Trail Run 10 km 50 km 100 km
November 2026
Nov
1
Su

8 Hours At The Farm

Trail Run 5 km 4 mi
Nov
8
Su

Raven Rocks Run

Trail Run 10 km 100 km
Nov
15
Su

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
21
Sa

Storybook Half Marathon

Trail Run 13 mi
Nov
26
Th

Soul N Body Thanksgiving Trail Run

Trail Run 4 mi
Nov
26
Th

Roxbury Thanksgiving Day Charity Race

Trail Run 5 km
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run 3 mi
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