Upcoming Races Near Plainville, CT - Matching: Trail Races

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

Hoppin Hodges Rails to Trails 5K

Andover, CT

Sunday, April 5th, 2026

Featured

Trail

View details for race Hoppin Hodges Rails to Trails 5K

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John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community Trail Race

11th Annual F.O.R 5k Trail Race

Wilbraham, MA

Sunday, April 12th, 2026

Trail

View details for race 11th Annual F.O.R 5k Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

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Brookhaven Trail 15K and 4 Mile Trail Run

Wading River, NY

Sunday, April 19th, 2026

15K

Trail

View details for race Brookhaven Trail 15K and 4 Mile Trail Run

Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

Trail

View details for race Tommy Sullivan's 5K

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

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2026 Deer Lake 5M Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

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Dandelion Dash and Mushroom Mile

Hadley, MA

Sunday, May 3rd, 2026

1 Mile

Trail

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

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Sgt. Joshua D. Desforges Walk/Run Challenge

Ludlow, MA

Saturday, May 9th, 2026

Trail

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Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

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Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

Trail

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

View details for race Oh Boy 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

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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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

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

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

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

Smile Like Jack 5k/10k/Fun Run

East Otis, MA

Saturday, July 11th, 2026

10K

Trail

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Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

View details for race Run for The Hills

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

Cockaponsett Trails to a Cure

Chester, CT

Sunday, September 20th, 2026

Trail

View details for race Cockaponsett Trails to a Cure

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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IronHike Series - Fall '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

View details for race IronHike Series - Fall '26

Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

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Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

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Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

View details for race Gemstone Sparkle Sprint 5k

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

View details for race Ivoryton Pumpkin Chase

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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Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

View details for race Frosty Forest 5k

Explore more in Plainville, CT

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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