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Upcoming Races Near Guilford, 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
Raven Rocks 10k Run and Raven 100k Challenge logo

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
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
Darien Depot Overstuffed Turkey Trot 5k and 1 Mile Fun Run logo

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

Darien, CT

Friday, November 28th, 2025

5K
1 Mile
Trail
View details for race Darien Depot Overstuffed Turkey Trot 5k and 1 Mile Fun Run
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
Tough Cookie 8K Trail Race logo

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 logo

SRC Presents: A Backyard Ultra

Hauppauge, NY

Saturday, December 13th, 2025

Trail
View details for race SRC Presents: A Backyard Ultra
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
Leatherman's Loop logo

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K
Trail
View details for race Leatherman's Loop
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 Guilford, CT

Distances:

5K10KHalf MarathonMarathon

Months:

OctoberNovemberDecember

Tags:

TrailBoston QualifiersFast Courses

State:

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