Upcoming Races Near Cheshire, CT - Matching: Trail Races

Name: Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk
Start: 2026-06-06
End: 2026-06-06
Location: Cornwall

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2025 Gulf Beach Half Marathon

Milford, CT

Saturday, September 13th, 2025

Half

Trail

View details for race 2025 Gulf Beach Half Marathon

Run for The Hills

Niantic, CT

Saturday, September 13th, 2025

Trail

View details for race Run for The Hills

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 14th, 2025

Trail

View details for race Where the Pavement Ends Single & Double Loop

3rd Annual Center Cancer Awareness Walk

Bridgehampton, NY

Saturday, September 20th, 2025

Trail

View details for race 3rd Annual Center Cancer Awareness Walk

Cockaponsett Trails to a Cure

Chester, CT

Sunday, September 21st, 2025

Trail

View details for race Cockaponsett Trails to a Cure

IronHike Series - Fall '25

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 2nd, 2025

Ultra

Trail

View details for race IronHike Series - Fall '25

IronHike Endurance Series - Fall 2025 - Mohawk ...

Cornwall, CT

Thursday, October 2nd, 2025

Ultra

Trail

View details for race IronHike Endurance Series - Fall 2025 - Mohawk Mtn, CT, USA

Chasing Ciara's Light 5k/12k Memorial Trail Race

Monroe, CT

Saturday, October 4th, 2025

12K

Trail

View details for race Chasing Ciara's Light 5k/12k Memorial Trail Race

2025 Rail Trail 10K Race

Hamden, CT

Saturday, October 4th, 2025

10K

Trail

View details for race 2025 Rail Trail 10K Race

Salmon River 5.5 Mile Run

Colchester, CT

Saturday, October 4th, 2025

Trail

Fast

View details for race Salmon River 5.5 Mile Run

Iron Hike - Fall Kuwohi Trail Half Marathon Plu...

Cornwall, CT

Saturday, October 4th, 2025

Trail

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

Together We Run for Education 5K Charity Road Race

East Hartford, CT

Saturday, October 4th, 2025

Trail

View details for race Together We Run for Education 5K Charity Road Race

Run Stanley

Westfield, MA

Sunday, October 5th, 2025

1 Mile

Trail

View details for race Run Stanley

Apple Harvest Road Races

Southington, CT

Sunday, October 5th, 2025

1 Mile

Trail

View details for race Apple Harvest Road Races

Norfolk Land Trust Trail Race Series/Haystack M...

Norfolk, CT

Sunday, October 5th, 2025

10K

Half

Trail

View details for race Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 11th, 2025

Trail

View details for race Gemstone Sparkle Sprint 5k

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 18th, 2025

Trail

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Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 18th, 2025

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Run The Farm

Katonah, NY

Sunday, October 19th, 2025

1 Mile

Trail

View details for race Run The Farm

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 25th, 2025

Trail

View details for race Collinsville Trick or Trot

Haunted Hustle

Waterford, CT

Sunday, October 26th, 2025

1 Mile

Trail

View details for race Haunted Hustle

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 26th, 2025

Trail

View details for race RACE FOR THE GREENWAY 5K RUN / WALK

Raven Rocks 10k Run and Raven 100k Challenge

Cross River, NY

Saturday, November 1st, 2025

10K

Trail

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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

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

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

View details for race Ion Bank Cheshire Road Races

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

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

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

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

September October November

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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