Trail Runs in New York — 2026

There are 36 trail runs in New York scheduled for 2026. The next is the Paine to Pain Trail Half Marathon in New Rochelle on October 11. New York trail runs run primarily October.

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 Closing Soon

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SUFFOLK COUNTY MARATHON

Sat, Oct 17 · BAY SHORE, NY BAY SHORE

1k KIDS FUN RUN5K FAMILY TRAIL RUN / WALK10K RUN +7

From $15 Open Closing Soon

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Ready, Set, Glow

Sat, Oct 17 · Victor, NY Victor

Short Course - FUN RUN!Ready Set GLOW

From $15 Closed

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Ganondagan Canicross and Dog-Friendly 5K Trail Race

Sat, Oct 17 · Victor, NY Victor

Canicross 5K RaceDog-Friendly Trail 5K Race

From $35 Open Closing Soon

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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 Closing Soon

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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 Closing Soon

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Hunt Hollow Colorfest Mountain Run

Sun, Oct 18 · Naples, NY Naples

Hunt Hollow Colorfest Family Run 3kHunt Hollow Colorfest Mountain Run 5k+

From $25 Open Closing Soon

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Hurds Farm After Dark 5K

Sat, Oct 24 · Modena, NY Modena

Little Kid Pumpkin Patch Dash 1KBig Kid Spooktacular 2KHurds Farm After Dark 5K

From $20 Open Closing Soon

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Annual STC Halloween Run

Sun, Oct 25 · FAYETTEVILLE, NY FAYETTEVILLE

Kid's Fun Run5K Trail Run

From $10 Open

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Trails, Tricks and Treats Race

Sun, Oct 25 · Painted Post, NY Painted Post

Trails, Tricks and Treats Race

From $25 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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Brantling Hill Rush

Sun, Nov 1 · Sodus, NY Sodus

3 Person Team

From $90 Open

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Saratoga Stryders Fall Back 5 Mile Trail Race

Sun, Nov 1 · Saratoga Springs, NY Saratoga Springs

5 Mile Trail Run

From $30 Open

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Clear Path 5k Trail Run

Sun, Nov 8 · Chittenango, NY Chittenango

Trail 5k

From $47.99 Open

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Dirt Cheap Stage Race presented by Darn Tough Vermont

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 $25 Open

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The Witching Hours 3/6/12/24H

Sat, Nov 14 · Manorville, NY Manorville

The Witching Hours 12 HourThe Witching Hours 3 Hour Night RunThe Witching Hours 24 Hour +2

From $70 Open 40 spots left

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Somers Track & Field Booster Club 8th Annual Thanksgiving Turkey Trot

Thu, Nov 26 · Somers, NY Somers

1 Mile Fun Run/Walk5K Race

From $15 Open

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SRC Presents: A Backyard Ultra

Sat, Dec 12 · Hauppauge, NY Hauppauge

The 1 LapperA Backyard Ultra

From $20 Open 100 spots left

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Snowy Owl Trail Race

Sun, Dec 13 · North Salem, NY North Salem

Snowy Owl Trail Race

From $37 Open Closing Soon

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King of The Hill

Sat, Mar 6 · Kings Park, NY Kings Park

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

From $60 Closed 30 spots left

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Big Bear SquaTCh North

Sat, Apr 3 · Bear Mountain, NY Bear Mountain

10K13.1M10K Ruck

From $45 Open

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John Jay Community Trail Race

Sun, Apr 4 · Cross River, NY Cross River

4k Jay Walk4k Jay Walk5k +3

From $13 Open

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Try the Trail

Sun, Apr 18 · Katonah, NY Katonah

0.5 Mile Trail Run0.5 Mile Trail Run1 Mile Trail Run +1

From $30 Closed

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Squatchywaska Mountainfest

Sat, Apr 24 · Ellenville, NY Ellenville

10M25K

From $70 Closed

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Leatherman's Loop

Sun, Apr 25 · Cross River, NY Cross River

Leatherman's LoopLeatherman's Loop

From $58 Closed

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Mother's Day 10K

Sat, May 8 · Lake Placid, NY Lake Placid

Mothers Day 5K RaceMothers Day 5K RaceMothers Day 10K Race +1

From $35 Closed

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Sand to Serengeti

Sun, May 16 · Fayetteville, NY Fayetteville

Sand to Serengeti - 3 Mile Trail RunSand to Serengeti - 5 Mile Trail RunSand to Serengeti - 10 Mile Trail Run +1

From $40 Closed 61 spots left

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Spring Run The Farm

Sun, May 23 · Katonah, NY Katonah

SPRING Kids Run The Farm (Race 1 - age 7-12 race)SPRING Kids Run The Farm (Race 1 - age 7-12 race)SPRING Run The Farm 5 Miler +3

From $20 Open

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Squatch the Hook

Sat, Jun 5 · Valley Cottage, NY Valley Cottage

5K Wheelchair Roll (Pavement)5K Run/Walk (Pavement)5K Wheelchair Roll (Pavement) +3

From $35 Open 10 spots left

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Fire Tower Trail Races

Sun, Jun 6 · Cross River, NY Cross River

Fire Tower 10k Trail RaceFire Tower 10k Trail RaceFire Tower Trail Half Marathon +1

From $45 Open

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YMCA Race Weekend

Sat, Jun 12 · Fayetteville, NY Fayetteville

YMCA Race Weekend 8K Trail RaceY-Challenge (For Saturday registrants Only) 8K Add onY-Challenge (For Saturday registrants Only) 8K Add on +13

From $0 Open 35 spots left

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Bowdoin Bushwhack Presented by Peace, Love, Trails

Wed, Jul 14 · Wappingers Falls, NY Wappingers Falls

5 Mile Trail Run5 Mile Trail Run

From $35 Closed 55 spots left

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Gardiner Dump Run

Sun, Sep 19 · Gardiner, NY Gardiner

Gardiner Dump Run 5kGardiner Dump Run 5kGardiner Dump Run 10k +2

From $5 Open

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Amy's Adventure Race for the Lake

Sat, Oct 2 · Bolton Landing, NY Bolton Landing

Amy's Adventure Race for the Lake (4.5 mile)Amy's Adventure Race for the Lake (Virtual)Amy's Adventure Race for the Lake (Virtual) +3

From $20 Open

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Big Bear SquaTCh South

Sat, Oct 16 · Tuxedo, NY Tuxedo

10K13.1M

From $45 Closed

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