Upcoming Races Near New Fairfield, CT - Matching: Trail Races

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

King of The Hill

Kings Park, NY

Saturday, March 7th, 2026

Featured

Trail

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SRC & Friends Supported Long Run

Wading River, NY

Sunday, March 15th, 2026

15K

Ultra

Trail

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Enchanted Forest Ultra Run

Stratford, CT

Saturday, March 21st, 2026

Trail

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Mudders and Grunters

Yorktown Heights, NY

Sunday, March 29th, 2026

Trail

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Sparrow's Nest Superhero Rock 'N' Run Challenge...

Poughquag, NY

Monday, March 30th, 2026

Ultra

Trail

View details for race Sparrow's Nest Superhero Rock 'N' Run Challenge and 5K

Joseph Ennesser 5K Run/Walk

Wappingers Falls, NY

Saturday, April 11th, 2026

Trail

View details for race Joseph Ennesser 5K Run/Walk

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

View details for race Ion Bank Cheshire Road Races

IBBC Trail Classic 5k and Kid's Trail Run prese...

Irvington, NY

Sunday, April 12th, 2026

Trail

View details for race IBBC Trail Classic 5k and Kid's Trail Run presented by Peace, Love, Trails

Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

Trail

View details for race Tommy Sullivan's 5K

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

Try the Trail

Katonah, NY

Sunday, April 26th, 2026

1 Mile

Trail

View details for race Try the Trail

2026 Deer Lake 5M Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

View details for race 2026 Deer Lake 5M Trail Run

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

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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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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

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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

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 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

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

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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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Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

View details for race Forbidden Forest 30 Hour Ultra

Paine to Pain Trail Half Marathon

New Rochelle, NY

Sunday, October 11th, 2026

Half

Trail

View details for race Paine to Pain Trail Half Marathon

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

View details for race Tom Centinaro Memorial "Dam" Race

FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

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Kiwanis Club of Newburgh Scholarship Run

Newburgh, NY

Sunday, October 25th, 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 New Fairfield, CT

Distances:

5K 10K Half Marathon Marathon

Months:

January February March

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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