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

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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

View details for race EDRRC - Pawling Moonlight Trail Run 5K

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

Bedford, NY

Sunday, June 28th, 2026

Trail

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EDRRC - Racing to Save Lives 5K/10K

Lagrangeville, NY

Sunday, July 5th, 2026

10K

Trail

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Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

Trail

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Pinky’s Rock n Rolla

Richmond Hill, NY

Saturday, July 11th, 2026

Trail

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Bowdoin Bushwhack Presented by Peace, Love, Trails

Wappingers Falls, NY

Wednesday, July 15th, 2026

Trail

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Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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The Perfect Ten & Five Mile Road Race

Hamden, CT

Saturday, August 1st, 2026

Trail

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The Hamden Combo

Hamden, 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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Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

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Trail Night NYC

Richmond Hill, NY

Thursday, August 13th, 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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Shore 2 The Pour Beach Run 2026

Stratford, CT

Saturday, August 22nd, 2026

Trail

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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)

2026 Ossining MATTERS Run-Walk for Education Fu...

Ossining, NY

Saturday, September 5th, 2026

Trail

View details for race 2026 Ossining MATTERS Run-Walk for Education Fundraiser

2026 Gulf Beach Half Marathon

Milford, CT

Saturday, September 12th, 2026

Half

Trail

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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

Where the Pavement Ends Single & Double Loop

Ridgefield, 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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17th Annual Farmington River Run 5K Trail Race

Farmington, CT

Sunday, September 20th, 2026

Trail

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Palisades Half Marathon + 6K Trail Run

Fort Lee, NJ

Sunday, September 27th, 2026

Half

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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2026 Rail Trail 10K Race

Hamden, CT

Saturday, October 3rd, 2026

10K

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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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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Paine to Pain Trail Half Marathon

New Rochelle, NY

Sunday, October 11th, 2026

Half

Trail

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Hope Children's Fund 22nd Annual Larry Hohler B...

Shoreham, NY

Saturday, October 17th, 2026

Trail

View details for race Hope Children's Fund 22nd Annual Larry Hohler Bi-Continental 5k Fun Run/Walk

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

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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RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, 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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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

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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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ROB'S TRAIL RUN EDITION

Woodbury, NY

Sunday, November 29th, 2026

Trail

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SRC Presents: A Backyard Ultra

Hauppauge, NY

Saturday, December 12th, 2026

Trail

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Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

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