61 Upcoming Races Near Pleasantville, NY - Matching: Trail Races

Diplo's Run Club New York

Queens, NY

Saturday, October 24th, 2026

Featured

Code:FTR10

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EDRRC - Racing to Save Lives 5K/10K

Lagrangeville, NY

Sunday, July 5th, 2026

10K

Trail

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Shawangunk Runners Summer XC Series

New Paltz, NY

Monday, July 6th, 2026

Trail

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52nd Summer XC Series

Gardiner, NY

Monday, July 6th, 2026

Trail

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Trail Night NJ

West Orange, NJ

Wednesday, July 8th, 2026

1 Mile

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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Montclair Run-cation

Montclair, NJ

Sunday, July 12th, 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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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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The Perfect Ten & Five Mile Road Race

Hamden, 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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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

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Barn-B-Q Trail Festival

Berkeley Heights, NJ

Saturday, September 5th, 2026

Trail

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

Ossining, NY

Saturday, September 5th, 2026

Trail

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Pompton Lakes 5K Run

Pompton Lakes, NJ

Sunday, September 6th, 2026

Trail

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2026 Gulf Beach Half Marathon

Milford, CT

Saturday, September 12th, 2026

Half

Trail

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FallApple

South Orange, NJ

Saturday, September 12th, 2026

10K

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

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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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NJ Trail Series One Day

Augusta, NJ

Thursday, October 1st, 2026

1 Mile

Ultra

Marathon

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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Point to Point NJ

Sussex, NJ

Friday, October 9th, 2026

Ultra

Trail

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Rocky's 5K

Pleasantville, NY

Saturday, October 10th, 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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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

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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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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Run the Woods 5k

Oak Ridge, NJ

Sunday, November 15th, 2026

1 Mile

Trail

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Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half

Trail

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Roxbury Road Race Series #35

Roxbury, CT

Saturday, November 21st, 2026

Trail

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FEAR Trail Fest 2026

Morristown, NJ

Sunday, November 22nd, 2026

Trail

Fast

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ROB'S TRAIL RUN EDITION

Woodbury, NY

Sunday, November 29th, 2026

Trail

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NJ Trail Series SOMO Winter 2

South Orange, NJ

Saturday, December 5th, 2026

10K

Half

Trail

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