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Upcoming Races Near Madison, CT - Matching: Trail Races

2025 Rail Trail 10K Race

Hamden, CT

Saturday, October 4th, 2025

Featured

10K

Trail

View details for race 2025 Rail Trail 10K Race

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Salmon River 5.5 Mile Run

Colchester, CT

Saturday, October 4th, 2025

Trail

Fast

View details for race Salmon River 5.5 Mile Run

Together We Run for Education 5K Charity Road Race

East Hartford, CT

Saturday, October 4th, 2025

5K

Trail

View details for race Together We Run for Education 5K Charity Road Race

Run for the Pumpkins Trail Run

Westerly, RI

Saturday, October 4th, 2025

10K

5K

Trail

View details for race Run for the Pumpkins Trail Run

Chasing Ciara's Light 5k/12k Memorial Trail Race

Monroe, CT

Saturday, October 4th, 2025

5K

12K

Trail

View details for race Chasing Ciara's Light 5k/12k Memorial Trail Race

Apple Harvest Road Races

Southington, CT

Sunday, October 5th, 2025

5K

1 Mile

Trail

View details for race Apple Harvest Road Races

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 18th, 2025

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 18th, 2025

5K

Trail

View details for race Ivoryton Pumpkin Chase

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 25th, 2025

5K

Trail

View details for race Collinsville Trick or Trot

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

Haunted Hustle

Waterford, CT

Sunday, October 26th, 2025

5K

1 Mile

Trail

View details for race Haunted Hustle

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

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

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

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

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

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

Peconic, NY

Sunday, July 26th, 2026

5K

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K

Trail

View details for race Run for The Hills

Explore more in Madison, 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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