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

RACE FOR THE GREENWAY 5K RUN / WALK logo

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 26th, 2025

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

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Haunted Hustle logo

Haunted Hustle

Waterford, CT

Sunday, October 26th, 2025

5K
1 Mile
Trail
View details for race Haunted Hustle
Pawtuxet River 5k: Run of the Mills logo

Pawtuxet River 5k: Run of the Mills

Coventry, RI

Saturday, November 1st, 2025

5K
Trail
View details for race Pawtuxet River 5k: Run of the Mills
Stonington Vineyards Wine Run Turkey Trot 5k logo

Stonington Vineyards Wine Run Turkey Trot 5k

Stonington, CT

Sunday, November 2nd, 2025

5K
Trail
View details for race Stonington Vineyards Wine Run Turkey Trot 5k
The Witching Hours 3/6/12H logo

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 logo

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
JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN logo

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
Ion Bank Cheshire Road Races logo

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half
5K
Trail
Fast
View details for race Ion Bank Cheshire Road Races
Run the Vineyards - Memorial Day at Pindar 5K logo

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

5K
1 Mile
Trail
View details for race Run the Vineyards - Memorial Day at Pindar 5K
Run the Vineyards - Pindar Vineyards 5K logo

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

5K
Trail
View details for race Run the Vineyards - Pindar Vineyards 5K
Run for The Hills logo

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K
Trail
View details for race Run for The Hills

Explore more in Old Saybrook, CT

Distances:

5K10KHalf MarathonMarathon

Months:

OctoberNovemberDecember

Tags:

TrailBoston QualifiersFast Courses

State:

All Connecticut races

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