Trail Runs in & near Oyster Bay, New York 2026 - 2027

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Trail Runs Found In Oyster Bay, New York

The most comprehensive list of Trail Runs in and near Oyster Bay, New York in 2026 - 2027. Find your perfect race!

Brookhaven, New York

BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Sun, Nov 15

from $39.48

Bronx, New York

The VCTC Pete McArdle 9-mile XC Trail Race

Sat, Nov 28

$38.10

Woodbury, New York

Rob's Trail Run Edition

Sun, Nov 29

from $44.00

Kings Park, New York

Tough Cookie 8k Trail Race

Sun, Dec 6

$33.80

Smithtown, New York

SRC Presents: A Backyard Ultra

Sat, Dec 12–13

from $33.80

North Salem, New York

Snowy Owl Trail Race

Sun, Dec 13

$40.22

Kings Park, New York

King of The Hill

Sat, Mar 6, 2027

from $75.20

Bear Mountain, New York

Big Bear SquaTCh North

Sat, Apr 3, 2027

Free–$75.20

Cross River, New York

John Jay Community Trail Race

Sun, Apr 4, 2027

from $15.84

Katonah, New York

Try the Trail

Sun, Apr 18, 2027

$32.80

New Rochelle, New York

Paine to Pain Trail Half Marathon

Thu, Apr 22 – Sep 26, 2027

Free

Ellenville, New York

Squatchywaska Mountainfest

Sat, Apr 24, 2027

Free–$80.50

Cross River, New York

Leatherman's Loop

Sun, Apr 25, 2027

$62.48

Katonah, New York

Spring Run The Farm

Sun, May 23, 2027

from $22.20

Valley Cottage, New York

Squatch the Hook

Sat, Jun 5, 2027

Free–$48.70

Cross River, New York

Fire Tower Trail Races

Sun, Jun 6, 2027

from $45.00

Wappingers Falls, New York

Bowdoin Bushwhack Presented by Peace, Love, Trails

Wed, Jul 14, 2027

$35.00

Gardiner, New York

Gardiner Dump Run

Sun, Sep 19, 2027

from $35.00

Tuxedo, New York

Big Bear SquaTCh South

Sat, Oct 16, 2027

Free–$69.90

Katonah, New York

FALL Run The Farm

Sun, Oct 24, 2027

from $22.20

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