Upcoming Races Near Fairfield, CT - Matching: Trail Races

Name: Frosty Forest 5k
Start: 2026-12-19
End: 2026-12-19
Location: Stratford

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

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Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

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MRCC/Trail Conference 5K

Mahwah, NJ

Sunday, May 17th, 2026

Trail

View details for race MRCC/Trail Conference 5K

Nassau Suffolk Trail Marathon & 15 Miler

Farmingdale, NY

Sunday, May 17th, 2026

Marathon

Trail

View details for race Nassau Suffolk Trail Marathon & 15 Miler

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

Fast

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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

11th Annual Flanders Field & Forest 5K Trail R...

Woodbury, CT

Friday, June 5th, 2026

Trail

View details for race 11th Annual Flanders Field & Forest 5K Trail Run/Walk

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

Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

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Fire Tower Trail Races

Cross River, NY

Sunday, June 7th, 2026

Half

10K

Trail

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Run in the Park 5K - to benefit the Milford Rot...

Milford, CT

Sunday, June 7th, 2026

Trail

View details for race Run in the Park 5K - to benefit the Milford Rotary and the Beth-El Center

Shirley Chisholm Trail Run 5K

Brooklyn, NY

Sunday, June 7th, 2026

Trail

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Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

View details for race EDRRC - Pawling Moonlight Trail Run 5K

Fork In The Trail 5k Presented By Peace, Love, ...

Bedford, NY

Sunday, June 28th, 2026

Trail

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Pinky’s Rock n Rolla

Richmond Hill, NY

Saturday, July 11th, 2026

Trail

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Bowdoin Bushwhack Presented by Peace, Love, Trails

Wappingers Falls, NY

Wednesday, July 15th, 2026

Trail

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Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

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Raptor Ridge Presented by Peace, Love, Trails (...

Mount Kisco, NY

Sunday, August 23rd, 2026

10K

Trail

View details for race Raptor Ridge Presented by Peace, Love, Trails (formerly the Sanctuary 6.5)

South Nyack 10-Miler

Nyack, NY

Saturday, September 5th, 2026

10 Miles

Trail

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Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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Cockaponsett Trails to a Cure

Chester, CT

Sunday, September 20th, 2026

Trail

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17th Annual Farmington River Run 5K Trail Race

Farmington, CT

Sunday, September 20th, 2026

Trail

View details for race 17th Annual Farmington River Run 5K Trail Race

Palisades Half Marathon + Trail Run

Fort Lee, NJ

Sunday, September 27th, 2026

Half

Trail

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IronHike Series - Fall '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

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Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

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Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

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4 in the Forest-April 6th, 2025-Irvington, NY

Irvington, NY

Sunday, October 4th, 2026

Trail

View details for race 4 in the Forest-April 6th, 2025-Irvington, NY

Paine to Pain Trail Half Marathon

New Rochelle, NY

Sunday, October 11th, 2026

Half

Trail

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Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

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Kiwanis Club of Newburgh Scholarship Run

Newburgh, NY

Sunday, October 25th, 2026

Trail

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RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 25th, 2026

Trail

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FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

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Hamden Hall Middle School Invitational

Hamden, CT

Wednesday, October 28th, 2026

Trail

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Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

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Raven Events

Cross River, NY

Sunday, November 1st, 2026

10K

Trail

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Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half

Trail

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ROB'S TRAIL RUN EDITION

Woodbury, NY

Sunday, November 29th, 2026

Trail

View details for race ROB'S TRAIL RUN EDITION

Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

View details for race Frosty Forest 5k

Explore more in Fairfield, CT

Distances:

5K 10K Half Marathon Marathon

Months:

May June July

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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