Upcoming Races Near Woodbury, 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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Run For The Shamrock

Hamden, CT

Sunday, March 15th, 2026

Trail

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Enchanted Forest Ultra Run

Stratford, CT

Saturday, March 21st, 2026

Trail

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ANDREW'S TOP GUN RUN 5K

Calverton, NY

Saturday, March 28th, 2026

Trail

Fast

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Jose's Jog

Wolcott, CT

Sunday, March 29th, 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

Wednesday, April 1st, 2026

Ultra

Trail

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

Hoppin Hodges Rails to Trails 5K

Andover, CT

Sunday, April 5th, 2026

Trail

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Joseph Ennesser 5K Run/Walk

Wappingers Falls, NY

Saturday, April 11th, 2026

Trail

View details for race Joseph Ennesser 5K Run/Walk

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

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

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Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

Trail

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Try the Trail

Katonah, NY

Sunday, April 26th, 2026

1 Mile

Trail

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2026 Deer Lake 5 Mile Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

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Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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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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Peach Hill "Run For the Hill of It" 5K

Poughkeepsie, NY

Saturday, May 30th, 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

The Big Run 5K/10K - Fleet Feet Poughkeepsie

Poughkeepsie, NY

Wednesday, June 3rd, 2026

10K

Trail

Fast

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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

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

Celebrate! West Hartford FUNd RUNS

West Hartford, CT

Sunday, June 7th, 2026

Trail

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Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

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Smile Like Jack 5k/10k/Fun Run

East Otis, MA

Saturday, July 11th, 2026

10K

Trail

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South Nyack 10-Miler

Nyack, NY

Saturday, September 5th, 2026

10 Miles

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

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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Gardiner Dump Run

Gardiner, NY

Sunday, September 27th, 2026

10K

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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Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

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Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

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Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

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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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Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

View details for race Frosty Forest 5k

Explore more in Woodbury, CT

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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