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

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Solstice Sprint 5K

West Hartford, CT

Wednesday, June 17th, 2026

Trail

Fast

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2026 Camp Jewell 5K Fun Run/Walk & Kids 1M

Colebrook, CT

Saturday, June 20th, 2026

1 Mile

Trail

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Roxbury Road Race Series #16

Roxbury, CT

Saturday, June 20th, 2026

Trail

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Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

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EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

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

Bedford, NY

Sunday, June 28th, 2026

Trail

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52nd Summer XC Series

Gardiner, NY

Monday, July 6th, 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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PATTERSONS PELLET—53rd Summer Series Week Two

Kerhonkson, NY

Monday, July 13th, 2026

1 Mile

Trail

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Bowdoin Bushwhack Presented by Peace, Love, Trails

Wappingers Falls, NY

Wednesday, July 15th, 2026

Trail

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Annual 5K Gardiner Classic Run/Walk

Gardiner, NY

Thursday, July 16th, 2026

Trail

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BLUEBERRY RUN—52nd Summer Series Week Three

Kerhonkson, NY

Monday, July 20th, 2026

1 Mile

Trail

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LOU’S RUN—53rd Summer Series Week Four

High Falls, NY

Monday, July 27th, 2026

1 Mile

Trail

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Pete Hawley People's 7

Barkhamsted, CT

Saturday, August 1st, 2026

Trail

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It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

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2nd Annual Rocky Hill 2M Run & Kids Run

Rocky Hill, CT

Saturday, August 15th, 2026

Trail

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PATH TO THE PARADE 5K

Hamden, CT

Friday, August 21st, 2026

Trail

Fast

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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

Sunday, September 13th, 2026

10 Miles

Trail

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KVIS 2026 Michael Berardino Memorial Road Race

Katonah, NY

Saturday, September 19th, 2026

1 Mile

Trail

View details for race KVIS 2026 Michael Berardino Memorial Road Race

2026 MHRRC Dutchess County Classic

Poughkeepsie, NY

Saturday, September 19th, 2026

Half

10K

Trail

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Where the Pavement Ends Single & Double Loop

Ridgefield, 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

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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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

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

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4 in the Forest Presented by Peace, Love, Trails

Irvington, NY

Sunday, October 4th, 2026

Trail

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Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

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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

Cheshire Community YMCA Harvest Trail Race and ...

Cheshire, CT

Saturday, October 24th, 2026

Trail

View details for race Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Kiwanis Club of Newburgh Scholarship Run

Newburgh, 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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Collinsville Trick or Trot

Collinsville, 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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Pocantico Hills Races

Tarrytown, NY

Saturday, November 7th, 2026

Marathon

Half

Trail

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Coach Mike Slinskey Memorial 5k

Wappingers Falls, NY

Sunday, November 8th, 2026

1 Mile

Trail

View details for race Coach Mike Slinskey Memorial 5k

Roxbury Road Race Series #35

Roxbury, CT

Saturday, November 21st, 2026

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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John Jay Community Trail Race

Cross River, NY

Sunday, April 4th, 2027

Trail

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Leatherman's Loop

Cross River, NY

Sunday, April 25th, 2027

10K

Trail

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