Upcoming Races Near Plainville, CT - Matching: Trail Races

Name: Leatherman's Loop
Start: 2027-04-25
End: 2027-04-25
Location: Cross River

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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Somers Summer Series

Somers, CT

Sunday, May 17th, 2026

Trail

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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

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

Fast

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Wayniacs Weekly Robinson Run

Agawam, MA

Tuesday, May 26th, 2026

Trail

View details for race Wayniacs Weekly Robinson Run

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

Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

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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

Celebrate! West Hartford FUNd RUNS

West Hartford, CT

Sunday, June 7th, 2026

Trail

View details for race Celebrate! West Hartford FUNd RUNS

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

Fire Tower Trail Races

Cross River, NY

Sunday, June 7th, 2026

Half

10K

Trail

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Solstice Sprint 5K

West Hartford, CT

Wednesday, June 17th, 2026

Trail

Fast

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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

Pirate's Beer Run! - A 0.5k Run For Cancer

Colchester, CT

Saturday, July 11th, 2026

Trail

View details for race Pirate's Beer Run! - A 0.5k Run For Cancer

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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It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

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Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

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Cockaponsett Trails to a Cure

Chester, CT

Sunday, September 20th, 2026

Trail

View details for race Cockaponsett Trails to a Cure

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

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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

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

View details for race Forbidden Forest 30 Hour Ultra

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Apple Harvest Road Races

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

Norfolk, CT

Sunday, October 4th, 2026

10K

Half

Trail

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

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Run Stanley

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

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Hamden Hall Middle School Invitational

Hamden, CT

Wednesday, October 28th, 2026

Trail

View details for race Hamden Hall Middle School Invitational

Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

View details for race Hamden Hall CISAC League Race

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

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Leatherman's Loop

Cross River, NY

Sunday, April 25th, 2027

10K

Trail

View details for race Leatherman's Loop

Explore more in Plainville, 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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