Trail Runs in New York — 2026

There are 33 trail runs in New York scheduled for 2026. The next is the Heckscher Classic 7 & 14 Mile Trail Race in East Islip on March 29. New York trail runs run primarily March through November.

King of The Hill

Sat, Mar 7 · Kings Park, NY Kings Park

King/Queen Of The Hill (3 Hours)Prince/Princess of the Hill (1 Hour)

From $60 Open 30 spots left

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Urban Environmental Challenge 10k

Sun, Mar 29 · Bronx, NY Bronx

10k

From $35 Open

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Heckscher Classic 7 & 14 Mile Trail Race

Sun, Mar 29 · East Islip, NY East Islip

Heckscher Classic 7 Mile Trail RaceHeckscher Classic 14 Mile Trail Race

From $45 Open

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John Jay Community Trail Race

Sun, Apr 12 · Cross River, NY Cross River

4k Jay Walk5kKids Jay Dash

From $13 Open Closing Soon

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

Sun, Apr 12 · Irvington, NY Irvington

Kid's Trail Run (10 and under)5k Trail Run/Walk

From $15 Open Closing Soon

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Try the Trail

Sun, Apr 26 · Katonah, NY Katonah

0.5 Mile Trail Run1 Mile Trail Run

From $30 Open

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Leatherman's Loop

Sun, Apr 26 · Cross River, NY Cross River

Leatherman's Loop

From $56 Closed

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Run our Trails

Tue, Apr 28 · Honeoye Falls, NY Honeoye Falls

Race 1- 3 Miles- Hopkins PointRace 6 - 3 Miles- Hopkins PointRace 2- 4 Miles- West Lodge +4

From $25 Open

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A Run to Remember

Sat, May 2 · Red Hook, NY Red Hook

5K Trail Run10k Trail Run

From $20 Open

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Medved Madness Trail Races

Sun, May 3 · Honeoye Falls, NY Honeoye Falls

Free Kid's K Trail RaceMedved Madness Short CourseMedved Madness Long Course +1

From $0 Open

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Mother's Day REXtravaganza

Sat, May 9 · Orangeburg, NY Orangeburg

3.75 mile REXtravaganza7.5 mile REXtravaganza11.25 mile REXtravaganza

From $30 Open

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Mother's Day 10K

Sat, May 9 · Lake Placid, NY Lake Placid

Mothers Day 5K RaceMothers Day 10K Race

From $35 Open

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Sehgahunda Trail Marathon, Marathon Relay & Vale of Three Falls

Sat, May 16 · Portageville, NY Portageville

Lower Falls 5KMiddle Falls 10KUpper Falls 15K +4

From $30 Open

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Spring Run The Farm

Sun, May 17 · Katonah, NY Katonah

SPRING Kids Run The Farm (Race 1 - age 7-12 race)SPRING Run The Farm 5 MilerSPRING Kids Run The Farm (Race 2 - age 6 & under race)

From $20 Open

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Sand to Serengeti

Sun, May 17 · Fayetteville, NY Fayetteville

Sand to Serengeti - 3 Mile Trail RunSand to Serengeti - 10 Mile Trail Run

From $40 Open 61 spots left

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Nassau Suffolk Trail Marathon & 15 Miler

Sun, May 17 · Farmingdale, NY Farmingdale

Nassau Suffolk Trail 15 MilerNassau Suffolk Trail Marathon

From $75 Open

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Highland Forest 1-2-3 Trail Run

Sat, May 23 · Fabius, NY Fabius

1 Loop (10 Miles)2 Loops (20 Miles)3 Loops (31 miles/50k)

From $25 Open

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Fleet Feet Dirt Cheap Trail Race Series

Wed, May 27 · Rochester, NY Rochester

Race 4 - Black Creek Park - Woodside LodgeDirt Cheap Trail Race Series (All 4 races)Race 1 - Durand Eastman Park - Magnolia Shelter +2

From $23 Open

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

Sat, May 30 · Poughkeepsie, NY Poughkeepsie

5K Walk/Run

From $20 Open

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Mendon Mauler Trail Races - 4 or 8 Miler

Fri, Jun 12 · Mendon, NY Mendon

4 Mile8 Mile

From $28 Open

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YMCA Race Weekend

Sat, Jun 13 · Fayetteville, NY Fayetteville

Y-Challenge (For Saturday registrants Only) 8K Add onYMCA Race Weekend 8K Trail RaceYMCA Race Weekend-Duathlon +5

From $0 Open 35 spots left

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Pinky’s Rock n Rolla

Sat, Jul 11 · Richmond Hill, NY Richmond Hill

4 Mile Trail Race

From $30 Open 100 spots left

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Swain Mountain Race

Sat, Aug 1 · Swain, NY Swain

Swain Mountain Race

From $50 Closed

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Newbsanity Extreme Ravine Trail Race

Sat, Aug 1 · Binghamton, NY Binghamton

5K15K12 Hour

From $35 Open

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Fellows Frolic

Sat, Aug 22 · Tully, NY Tully

Fellows Frolic -3 HourFellows Frolic -$1,000 Challenge

From $45 Open

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Serenity on the Trails

Sat, Aug 22 · Schenectady, NY Schenectady

Serenity on the Trails

From $35 Open

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Amy's Adventure Race for the Lake

Sat, Oct 3 · Bolton Landing, NY Bolton Landing

Amy's Adventure Race for the Lake (Virtual)Amy's Adventure Race for the Lake (4.5 mile)Amy's Adventure Race for the Lake (10 mile Loop)

From $20 Open

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Paine to Pain Trail Half Marathon

Sun, Oct 11 · New Rochelle, NY New Rochelle

Paine to Pain Trail Half MarathonClaim your NewRo Club Membership!

From $0 Closed

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Sunshine Camp Trail Mix & Beer Fest

Fri, Oct 16 · Rush, NY Rush

Sunshine Camp Trail Mix 5K & Beer FestSunshine Camp Trail Mix 5K (under 21 years old)

From $20 Open

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SUFFOLK COUNTY MARATHON

Sat, Oct 17 · BAY SHORE, NY BAY SHORE

1k KIDS FUN RUN5K FAMILY TRAIL RUN / WALK10K RUN +6

From $15 Open

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UR Skeleton Run

Sun, Oct 18 · Deerfield, NY Deerfield

Kids Quarter mile Run (3-12 year old)Skeleton Community Run (1.5 mile)Skeleton Run 5K (3.1 mile)

From $0 Open

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Malta 2K, 3K, 5k Trail Race

Sun, Oct 18 · Malta, NY Malta

2K Kids Trail Run3K Kids Trail Run5K Trail Run/Hike

From $15 Open

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FALL Run The Farm

Sun, Oct 25 · Katonah, NY Katonah

Fall Kids Run The Farm (Race 1 - age 7-12 race)Fall Run The Farm 5 MilerFall Kids Run The Farm (Race 2 - age 6 & under race)

From $20 Open

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Dirt Cheap Stage Race

Fri, Nov 13 · Mendon, NY Mendon

Stage 1 - Pond Road Time TrialStage 2 - Devil's Bathtub 5 MileStage 3 - The Epic Stage 11 Mile +1

From $23 Closed

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