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Trail Running Calendar near Newtown 2026-2027

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Explore the top trail runs near Newtown for 2026-2027! We've gathered 32 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep-Oct
16-24
We - Sa

Cheshire Community YMCA 5K Harvest Trail Run

Trail Run 5 km
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
October 2026
Oct
1-4
Th - Su

IronHike Endurance Series

Trail Run Backyard Ultra
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 Newtown

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Oct
3
Sa

Chasing Ciara's Light

Trail Run 5 km 12 km
Oct
10
Sa

Gemstone Sparkle Sprint 5k

Trail Run 3 mi
Oct
11
Su

Mohawk Mountain Race

Trail Run 5 km 10 km Half Marathon Marathon
Oct
17
Sa

Tom Centinaro Memorial "Dam" Race

Trail Run 4 mi
Oct
25
Su

Run The Farm - Katonah

Trail Run 5 mi
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
21
Sa

Fall Fling

Trail Run 4 mi 400 min
Nov
22
Su

Stride for the Knights 5K

Trail Run 5 km
Nov
22
Su

Head for the Hilltop 5K

Trail Run 5 km
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
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