57 Upcoming Races Near New Canaan, CT - Matching: Trail Races

Sun, Nov 11 race

Raven Events

Cross River, NY

10K

Sat, Nov 72 races

Pocantico Hills Races

Tarrytown, NY

Marathon, Half

VFW Post 6249 Suffolk County World War II and Military History Museum's "Rails to Trail" 5K

Rocky Point, NY

5K

Sun, Nov 82 races

Coach Mike Slinskey Memorial 5k

Wappingers Falls, NY

5K, 1 Mile

Woodbridge Trail Run + Woodland Walk

Woodbridge, CT

Sat, Nov 142 races

The Witching Hours 3/6/12/24H

Manorville, NY

NJ Trail Series SOMO Winter 1

South Orange, NJ

5K, 10K, Half

Sun, Nov 151 race

BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Wading River, NY

Half

Sat, Nov 213 races

Storybook Half Marathon

Stratford, CT

Half

Sargent Elementary 5K Turkey Trot

Beacon, NY

5K, 1 Mile

Roxbury Road Race Series #35

Roxbury, CT

Sun, Nov 223 races

Thunderbird Run 2026: Annual Mahwah Schools Foundation 5K Run, 2Mi Walk and Kids Run

MAHWAH, NJ

5K

Stride for the Knights 5K

Southington, CT

5K

Fri, Nov 271 race

Darien Depot Overstuffed Turkey Trot 5K and 1 Mile Fun Run

Darien, CT

5K, 1 Mile

Sun, Nov 291 race

ROB'S TRAIL RUN EDITION

Woodbury, NY

5K

Sat, Dec 53 races

NJ Trail Series SOMO Winter 2

South Orange, NJ

5K, 10K, Half

Woodburrr (no Y) 1-Miler

Woodbury, CT

1 Mile

JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Calverton, NY

5K

Sun, Dec 61 race

Tough Cookie 8K Trail Race

Kings Park, NY

Sat, Dec 121 race

SRC Presents: A Backyard Ultra

Hauppauge, NY

Sun, Dec 131 race

Snowy Owl Trail Race

North Salem, NY

Sat, Dec 192 races

Frosty Forest 5k

Stratford, CT

5K

New Canaan Santa Run

New Canaan, CT

5K, 1 Mile

Sat, Jan 9, 20271 race

NJ Trail Series SOMO Winter 3

South Orange, NJ

5K, 10K, Half

Sat, Jan 30, 20271 race

Frosty Squatchy

West Orange, NJ

5K

Sun, Feb 14, 20271 race

Squatchy Onesiefest

Mahwah, NJ

5K

Sat, Feb 20, 20271 race

Febapple Frozen 50M, 50K, 20M, 10M

South Orange, NJ

Ultra, 10 Miles

Sat, Mar 6, 20272 races

King of The Hill

Kings Park, NY

Squatchapple

West Orange, NJ

1 Mile, Ultra

Sun, Mar 28, 20271 race

Winter Series-Jose's Jog

Wolcott, CT

Sat, Apr 3, 20273 races

2027 Savin Rock Marathon & Half Marathon

West Haven, CT

Half, Marathon

2027 Shoreline Sharks 3 Half Marathon Ticket

West Haven, CT

Half

Big Bear SquaTCh North

Bear Mountain, NY

10K, Half

Sun, Apr 4, 20271 race

John Jay Community Trail Race

Cross River, NY

5K

Sun, Apr 11, 20271 race

Ion Bank Cheshire Road Races

Cheshire, CT

Half, 5K

Sun, Apr 18, 20271 race

Try the Trail

Katonah, NY

1 Mile

Thu, Apr 22, 20271 race

Paine to Pain Trail Half Marathon

New Rochelle, NY

Half

Sun, Apr 25, 20271 race

Leatherman's Loop

Cross River, NY

10K

Sat, May 8, 20271 race

2nd Annual Camp Mountain Laurel - Color Run & Trail Run

Hamden, CT

Sat, May 22, 20271 race

Feral Swan Trail Fest

Ringwood, NJ

1 Mile, 10K, Half

Sun, May 23, 20271 race

Spring Run The Farm

Katonah, NY

1 Mile

Sat, May 29, 20271 race

2027 Hamden Hills Half Marathon & Flat 5K

Hamden, CT

5K, Half

Thu, Jun 3, 20271 race

IronHike Mohawk Mountain Spring Series 2027

Mohawk Mtn Ski Area, Cornwall, CT

Ultra

Sat, Jun 5, 20271 race

Squatch the Hook

Valley Cottage, NY

10K, 5K

Sun, Jun 6, 20271 race

Fire Tower Trail Races

Cross River, NY

Half, 10K

Wed, Jul 14, 20271 race

Bowdoin Bushwhack Presented by Peace, Love, Trails

Wappingers Falls, NY

Sat, Jul 24, 20271 race

Squatchy Surprise

South Orange Village, NJ

5K, Half, Ultra

Sat, Jul 31, 20271 race

2027 Perfect Ten & Five Mile Road Race

Hamden, CT

Sat, Aug 14, 20271 race

Interstate 17

Closter, NJ