Upcoming Races Near Peekskill, NY - Matching: Trail Races

Name: Run the Woods 5k
Start: 2026-11-15
End: 2026-11-15
Location: Oak Ridge

Enchanted Forest Ultra Run

Stratford, CT

Saturday, March 21st, 2026

Featured

Trail

View details for race Enchanted Forest Ultra Run

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Urban Environmental Challenge 10k

Bronx, NY

Sunday, March 29th, 2026

10K

Trail

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Mudders and Grunters

Yorktown Heights, NY

Sunday, March 29th, 2026

Trail

View details for race Mudders and Grunters

Sparrow's Nest Superhero Rock 'N' Run Challenge...

Poughquag, NY

Wednesday, April 1st, 2026

Ultra

Trail

View details for race Sparrow's Nest Superhero Rock 'N' Run Challenge and 5K

Spring SOMO Timed Trail Races

South Orange, NJ

Saturday, April 4th, 2026

Trail

View details for race Spring SOMO Timed Trail Races

Joseph Ennesser 5K Run/Walk

Wappingers Falls, NY

Saturday, April 11th, 2026

Trail

View details for race Joseph Ennesser 5K Run/Walk

IBBC Trail Classic 5k and Kid's Trail Run prese...

Irvington, NY

Sunday, April 12th, 2026

Trail

View details for race IBBC Trail Classic 5k and Kid's Trail Run presented by Peace, Love, Trails

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community Trail Race

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

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Try the Trail

Katonah, NY

Sunday, April 26th, 2026

1 Mile

Trail

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XC Summer Series

Parsippany, NJ

Tuesday, April 28th, 2026

Trail

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Crotona Park 5K

Bronx, NY

Saturday, May 2nd, 2026

Trail

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

The Madison 5K Run/Walk

Madison, NJ

Sunday, May 3rd, 2026

Trail

View details for race The Madison 5K Run/Walk

Girls on the Run Spring 5K

Sparta, NJ

Saturday, May 16th, 2026

Trail

View details for race Girls on the Run Spring 5K

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

View details for race Forgotten Forest 9 Hour Ultra

MRCC/Trail Conference 5K

Mahwah, NJ

Sunday, May 17th, 2026

Trail

View details for race MRCC/Trail Conference 5K

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

Nassau Suffolk Trail Marathon & 15 Miler

Farmingdale, NY

Sunday, May 17th, 2026

Marathon

Trail

View details for race Nassau Suffolk Trail Marathon & 15 Miler

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

View details for race Oh Boy 5K

Randolph Rocks 5K and 1K Fun Run

Randolph, NJ

Saturday, May 30th, 2026

Trail

View details for race Randolph Rocks 5K and 1K Fun Run

Peach Hill "Run For the Hill of It" 5K

Poughkeepsie, NY

Saturday, May 30th, 2026

Trail

View details for race Peach Hill "Run For the Hill of It" 5K

IronHike Endurance Series - Spring 2026 - Mohaw...

Cornwall, CT

Wednesday, June 3rd, 2026

Ultra

Trail

View details for race IronHike Endurance Series - Spring 2026 - Mohawk Mtn, CT, USA

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

Poughkeepsie, NY

Wednesday, June 3rd, 2026

10K

Trail

Fast

View details for race The Big Run 5K/10K - Fleet Feet Poughkeepsie

IronHike Series - Spring '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, June 4th, 2026

Ultra

Trail

View details for race IronHike Series - Spring '26

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

Woodbury, CT

Friday, June 5th, 2026

Trail

View details for race 11th Annual Flanders Field & Forest 5K Trail Run/Walk

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

Trail

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

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

Milford, CT

Sunday, June 7th, 2026

Trail

View details for race Run in the Park 5K - to benefit the Milford Rotary and the Beth-El Center

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

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

Bedford, NY

Sunday, June 28th, 2026

Trail

View details for race Fork In The Trail 5k Presented By Peace, Love, Trails

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

View details for race Bowdoin Bushwhack Presented by Peace, Love, Trails

Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

View details for race Interstate 17

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

Saturday, September 5th, 2026

10 Miles

Trail

View details for race South Nyack 10-Miler

FallApple

South Orange, NJ

Saturday, September 12th, 2026

10K

Half

Trail

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Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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Gardiner Dump Run

Gardiner, NY

Sunday, September 27th, 2026

10K

Trail

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IronHike Series - Fall '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

View details for race IronHike Series - Fall '26

NJ Trail Series One Day

Augusta, NJ

Thursday, October 1st, 2026

1 Mile

Ultra

Marathon

Trail

View details for race NJ Trail Series One Day

Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

View details for race Forbidden Forest 30 Hour Ultra

4 in the Forest-April 6th, 2025-Irvington, NY

Irvington, NY

Sunday, October 4th, 2026

Trail

View details for race 4 in the Forest-April 6th, 2025-Irvington, NY

Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

View details for race Gemstone Sparkle Sprint 5k

Paine to Pain Trail Half Marathon

New Rochelle, NY

Sunday, October 11th, 2026

Half

Trail

View details for race Paine to Pain Trail Half Marathon

FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

View details for race FALL Run The Farm

Kiwanis Club of Newburgh Scholarship Run

Newburgh, NY

Sunday, October 25th, 2026

Trail

View details for race Kiwanis Club of Newburgh Scholarship Run

Strides for Education Hybrid 5K Run/Walk

Morris Plains, NJ

Sunday, October 25th, 2026

Trail

Fast

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Raven Events

Cross River, NY

Sunday, November 1st, 2026

10K

Trail

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NJ Trail Series SOMO Winter 1

South Orange, NJ

Saturday, November 14th, 2026

10K

Half

Trail

View details for race NJ Trail Series SOMO Winter 1

Run the Woods 5k

Oak Ridge, NJ

Sunday, November 15th, 2026

1 Mile

Trail

View details for race Run the Woods 5k

Explore more in Peekskill, NY

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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