Upcoming Races Near Litchfield, 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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EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

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Centurion Trail 33 Hour Ultra

Stratford, CT

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

Colchester, CT

Saturday, July 11th, 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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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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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

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KVIS 2026 Michael Berardino Memorial Road Race

Katonah, NY

Saturday, September 19th, 2026

1 Mile

Trail

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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

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Cockaponsett Trails to a Cure

Chester, 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

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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

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Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

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Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

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Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 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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Cheshire Community YMCA Harvest Trail Race and ...

Cheshire, CT

Saturday, October 24th, 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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Hamden Hall Middle School Invitational

Hamden, CT

Wednesday, October 28th, 2026

Trail

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Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

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Hamden Hall CISAC League Race

Hamden, 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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Coach Mike Slinskey Memorial 5k

Wappingers Falls, NY

Sunday, November 8th, 2026

1 Mile

Trail

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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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