Upcoming Races Near Old Greenwich, CT - Matching: Trail Races

Name: South Nyack 10-Miler
Start: 2026-09-05
End: 2026-09-05
Location: Nyack

Paine to Pain Trail Half Marathon

New Rochelle, NY

Sunday, October 12th, 2025

Featured

Half

Trail

View details for race Paine to Pain Trail Half Marathon

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2nd Annual Randolph School Ramble 5K Run/Walk

Wappingers Falls, NY

Sunday, October 12th, 2025

Trail

View details for race 2nd Annual Randolph School Ramble 5K Run/Walk

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 18th, 2025

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Kiwanis Club of Newburgh Scholarship Run

Newburgh, NY

Sunday, October 19th, 2025

Trail

View details for race Kiwanis Club of Newburgh Scholarship Run

Run The Farm

Katonah, NY

Sunday, October 19th, 2025

1 Mile

Trail

View details for race Run The Farm

Strides for Education Hybrid 5K Run/Walk

Morris Plains, NJ

Saturday, October 25th, 2025

Trail

Fast

View details for race Strides for Education Hybrid 5K Run/Walk

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 26th, 2025

Trail

View details for race RACE FOR THE GREENWAY 5K RUN / WALK

Thunderbird Run 2025: Annual Mahwah Schools Fou...

MAHWAH, NJ

Sunday, October 26th, 2025

Trail

View details for race Thunderbird Run 2025: Annual Mahwah Schools Foundation 5K Run, 2Mi Walk and Kids Run

Coach Mike Slinskey Celebration of Life 5k

Wappingers Falls, NY

Monday, October 27th, 2025

1 Mile

Trail

View details for race Coach Mike Slinskey Celebration of Life 5k

Raven Rocks 10k Run and Raven 100k Challenge

Cross River, NY

Saturday, November 1st, 2025

10K

Trail

View details for race Raven Rocks 10k Run and Raven 100k Challenge

NJ Trail Series SOMO Winter 1

South Orange, NJ

Saturday, November 15th, 2025

10K

Half

Trail

View details for race NJ Trail Series SOMO Winter 1

Run the Woods 5k

Oak Ridge, NJ

Saturday, November 15th, 2025

1 Mile

Trail

View details for race Run the Woods 5k

The Witching Hours 3/6/12H

Manorville, NY

Saturday, November 15th, 2025

Trail

View details for race The Witching Hours 3/6/12H

BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Wading River, NY

Sunday, November 16th, 2025

Half

Trail

View details for race BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Head for the Hilltop 5K + Kids Fun Run

Yorktown Heights, NY

Sunday, November 23rd, 2025

Trail

View details for race Head for the Hilltop 5K + Kids Fun Run

Darien Depot Overstuffed Turkey Trot 5k and 1 M...

Darien, CT

Friday, November 28th, 2025

1 Mile

Trail

View details for race Darien Depot Overstuffed Turkey Trot 5k and 1 Mile Fun Run

ROB'S TRAIL RUN EDITION

Woodbury, NY

Sunday, November 30th, 2025

Trail

View details for race ROB'S TRAIL RUN EDITION

JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Calverton, NY

Saturday, December 6th, 2025

Trail

View details for race JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Tough Cookie 8K Trail Race

Kings Park, NY

Sunday, December 7th, 2025

Trail

Fast

View details for race Tough Cookie 8K Trail Race

SRC Presents: A Backyard Ultra

Hauppauge, NY

Saturday, December 13th, 2025

Trail

View details for race SRC Presents: A Backyard Ultra

Morris Hot Cocoa 5K 12/13 10 am

Morris Plains, NJ

Saturday, December 13th, 2025

Trail

View details for race Morris Hot Cocoa 5K 12/13 10 am

NJ Trail Series SOMO Winter 2

South Orange, NJ

Saturday, December 13th, 2025

10K

Half

Trail

View details for race NJ Trail Series SOMO Winter 2

NJ Trail Series SOMO Winter 3

South Orange, NJ

Saturday, January 10th, 2026

10K

Half

Trail

View details for race NJ Trail Series SOMO Winter 3

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

South Orange, NJ

Saturday, February 21st, 2026

Ultra

10 Miles

Trail

View details for race Febapple Frozen 50M, 50K, 20M, 10M

Spring SOMO Timed Trail Races

South Orange, NJ

Saturday, April 11th, 2026

Trail

View details for race Spring SOMO Timed Trail Races

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

View details for race Ion Bank Cheshire Road Races

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

View details for race Leatherman's Loop

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

View details for race Interstate 17

South Nyack 10-Miler

Nyack, NY

Saturday, September 5th, 2026

10 Miles

Trail

View details for race South Nyack 10-Miler

Explore more in Old Greenwich, CT

Distances:

5K 10K Half Marathon Marathon

Months:

October November December

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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