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Upcoming Races Near Cheshire, CT - Matching: Trail Races

Raven Rocks 10k Run and Raven 100k Challenge

Cross River, NY

Saturday, November 1st, 2025

Featured

10K

Trail

View details for race Raven Rocks 10k Run and Raven 100k Challenge

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The Witching Hours 3/6/12H

Manorville, NY

Saturday, November 15th, 2025

Trail

View details for race The Witching Hours 3/6/12H

BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Wading River, NY

Sunday, November 16th, 2025

Half

Trail

View details for race BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Head for the Hilltop 5K + Kids Fun Run

Yorktown Heights, NY

Sunday, November 23rd, 2025

5K

Trail

View details for race Head for the Hilltop 5K + Kids Fun Run

Soul n Body Thanksgiving 5k

Wolcott, CT

Thursday, November 27th, 2025

Trail

View details for race Soul n Body Thanksgiving 5k

Darien Depot Overstuffed Turkey Trot 5k and 1 M...

Darien, CT

Friday, November 28th, 2025

5K

1 Mile

Trail

View details for race Darien Depot Overstuffed Turkey Trot 5k and 1 Mile Fun Run

JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Calverton, NY

Saturday, December 6th, 2025

Trail

View details for race JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Tough Cookie 8K Trail Race

Kings Park, NY

Sunday, December 7th, 2025

Trail

Fast

View details for race Tough Cookie 8K Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

5K

Trail

Fast

View details for race Ion Bank Cheshire Road Races

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

5K

Trail

View details for race John Jay Community Trail Race

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

View details for race Leatherman's Loop

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

5K

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

IronHike Endurance Series - Spring 2026 - Mohaw...

Cornwall, CT

Wednesday, June 3rd, 2026

Ultra

Trail

View details for race IronHike Endurance Series - Spring 2026 - Mohawk Mtn, CT, USA

IronHike Series - Spring '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, June 4th, 2026

Ultra

Trail

View details for race IronHike Series - Spring '26

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

Trail

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

5K

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K

Trail

View details for race Run for The Hills

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

October November December

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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