Upcoming Races Near Westchester County, NY - Matching: Trail Races

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Featured

Trail

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Roxbury Road Race Series #13

Roxbury, CT

Saturday, May 30th, 2026

Trail

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Randolph Rocks 5K and 1K Fun Run

Randolph, NJ

Saturday, May 30th, 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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Pinkathon 2026 Virtual and In-Person Challenge ...

Any Place in the World!, CA

Monday, June 1st, 2026

10K

10 Miles

Trail

View details for race Pinkathon 2026 Virtual and In-Person Challenge for Breast Cancer!

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

Poughkeepsie, NY

Wednesday, June 3rd, 2026

10K

Trail

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11th Annual Flanders Field & Forest 5K Trail R...

Woodbury, CT

Friday, June 5th, 2026

Trail

Fast

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Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

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Squatchy Hooky: Lake to Summit

Valley Cottage, NY

Saturday, June 6th, 2026

10K

Trail

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Rockwood Ramble 10K

Sleepy Hollow, NY

Saturday, June 6th, 2026

10K

Trail

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Shirley Chisholm Trail Run 5K

Brooklyn, NY

Sunday, June 7th, 2026

Trail

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Run in the Park 5K - to benefit the Milford Rot...

Milford, CT

Sunday, June 7th, 2026

Trail

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Fire Tower Trail Races

Cross River, NY

Sunday, June 7th, 2026

Half

10K

Trail

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52nd Annual Rooster Run

Newtown, CT

Saturday, June 13th, 2026

10K

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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5K Race for Recovery 4th of July

Central Park of Morris County, Parsippany-Troy Hills, NJ

Saturday, July 4th, 2026

Trail

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Trail Night NJ

West Orange, NJ

Wednesday, July 8th, 2026

1 Mile

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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Annual 5K Gardiner Classic Run/Walk

Gardiner, NY

Thursday, July 16th, 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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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

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South Nyack 10-Miler

Nyack, NY

Saturday, September 5th, 2026

10 Miles

Trail

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Pompton Lakes 5K Run

Pompton Lakes, NJ

Sunday, September 6th, 2026

Trail

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FallApple

South Orange, NJ

Saturday, September 12th, 2026

10K

Half

Trail

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2026 Gulf Beach Half Marathon

Milford, CT

Saturday, September 12th, 2026

Half

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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Palisades Half Marathon + Trail Run

Fort Lee, NJ

Sunday, September 27th, 2026

Half

Trail

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Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

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

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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

Strides for Education Hybrid 5K Run/Walk

Morris Plains, NJ

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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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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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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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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NJ Trail Series SOMO Winter 1

South Orange, NJ

Saturday, November 14th, 2026

10K

Half

Trail

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Explore more in Westchester County, NY

Distances:

5K 10K Half Marathon Marathon

Months:

May June July

Tags:

Trail Boston Qualifiers Fast Courses

State:

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